Name: 203065-88-7|2-(4-(Trifluoromethyl)phenyl)pyridine|98%
Brand: Ambeed
SKU: A157722
Price: 26.0 USD
Availability: InStock
Rating: 98 (28 reviews)

1
[ 109-09-1 ]
[ 98-56-6 ]
[ 203065-88-7 ]

Yield	Reaction Conditions	Operation in experiment
83%	With manganese; nickel bromide 2,2’-bipyridine complex; trifluoroacetic acid In N,N-dimethyl-formamide at 20℃; for 3h;
63%	With (2,2'-bipyridine)nickel(II) dibromide; tetrabutylammonium tetrafluoroborate In N,N-dimethyl-formamide Ambient temperature; electrolysis;

Reference： [1]Location in patent: experimental part Gosmini, Corinne; Bassene-Ernst, Carine; Durandetti, Muriel [Tetrahedron, 2009, vol. 65, # 31, p. 6141 - 6146]
[2]Gosmini, Corinne; Lasry, Sarah; Nedelec, Jean-Yves; Perichon, Jacques [Tetrahedron, 1998, vol. 54, # 7, p. 1289 - 1298]

2
[ 109-09-1 ]
[ 128796-39-4 ]
[ 203065-88-7 ]

Yield	Reaction Conditions	Operation in experiment
67%	With palladium diacetate; potassium carbonate; triphenylphosphine In 1,2-dimethoxyethane Inert atmosphere; Reflux;	General procedure A for the synthesis of ligands (2b-2g). General procedure: To a two necked, 100 mL round bottom flask equipped with a magnetic stir bar were added 2-chloropyridine (1 equiv), phenylboronic acid (1.2 equiv), triphenylphosphine (0.1 equiv), 2 M potassium carbonate (2.7 equiv) and ethylene glycol dimethyl ether(0.9 M). The mixture was degased with Ar for 15 min. Then Pd(OAc)2 (2.5 mol%) was added to the reaction mixture and degassing continued for 15 more minutes and then the outlet was removed. The reaction mixture was heated to reflux. The progress of reaction was monitored by TLC (hexane:EtOAc 90:10). Upon completion (typically 18-24 h), reaction mixture was cooled to room temperature and then extracted with DCM (3x20 mL). The combined organic portion was washed with water (3x20 mL) and brine (1 20 mL), dried over anhydrous sodium sulfate and then concentrated in vacuo. The crude material was purified by flash chromatography to obtain pure ligand.
63%	With water; potassium carbonate In 1,2-dimethoxyethane for 18h; Heating;
54%	With potassium phosphate In ethanol; water at 100℃; for 8h;	2.4. General procedure for Suzuki coupling reaction catalyzed bypolymer anchored-Pd(II) D General procedure: A dried round bottomed flask equipped with a magnetic stirring bar was charged with 10mg Polymer anchored-Pd(II) D catalyst (PS-NPPZ-Pd) (0.0045mmol/Pd), 2-halopyridine (0.5mmol), phenylboronic acid (0.6mmol) and K3PO4 (1.0mmol) were added to a reaction vessel. The mixture was stirred in 4mL of H2O: EtOH (1:1) at 100°C for 8h and then cooled to room temperature. The catalyst was filtered and the filtrate was extracted with ethyl acetate (3×10mL). The combined organic layers were extracted with water, and dried over anhydrous Na2SO4. The organic layers were evaporated under reduced pressure and the resulting crude product was purified by column chromatography by using ethyl acetate/hexane (10:90) as eluent to give the corresponding coupled products. The products were characterized by 1H NMR, 13C NMR and HRMS analysis.

Reference： [1]Singh, Anuradha; Teegardin, Kip; Kelly, Megan; Prasad, Kariate S.; Krishnan, Sadagopan; Weaver, Jimmie D. [Journal of Organometallic Chemistry, 2015, vol. 776, p. 51 - 59]
[2]Lohse, Olivier; Thevenin, Philippe; Waldvogel, Erwin [Synlett, 1999, # 1, p. 45 - 48]
[3]Perumgani, Pullaiah C.; Kodicherla, Balaswamy; Mandapati, Mohan Rao; Parvathaneni, Sai Prathima [Inorganica Chimica Acta, 2018, vol. 477, p. 227 - 232]

3
[ 203065-88-7 ]
2-(2-chloro-4-(trifluoromethyll)phenyl)pyridine [ No CAS ]
2-(2,6-dichloro-4-(trifluoromethyll)phenyl)pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1: 78% 2: 3%	With copper(II) nitrate trihydrate; oxygen; acetic acid; lithium chloride at 150℃; for 24h; Sealed tube;
1: 58% 2: 23%	With chromium(VI) oxide; copper(II) nitrate trihydrate; acetic anhydride; acetic acid; lithium chloride at 150℃; for 48h; sealed tube;
1: 42% 2: 20%	With oxygen; copper dichloride In 1,2-dichloro-ethane at 130℃; for 24h;

1: 42% 2: 20%

With oxygen; 1,1,2,2-tetrachloroethane at 130℃; for 24h;

14 EXAMPLE 14; Synthesis of 2-(2-chloro-4-(trifluoromethyl)phenyl)pyridine (6a) and 2-(2,6-dichloro-4-(trifluoromethyl)phenyl)pyridine (6b)In a 40 mL tube, 2-(4-trifluoromethylphenyl)pydrine (0.3 mmol, 1 equiv) and CuCl2 (8.1 mg, 0.06 mmol, 20% equiv) were dissolved in 1 mL of Cl2CHCHCb under oxygen. The tube was sealed with a Teflon lined cap, and the reaction mixture was stirred at 1300C for 24 h. The reaction mixture was diluted with 20 mL of CH2Cl2 and then treated with 10 mL of saturated Na2S aqueous solution. The mixture was filtered through a pad of Celite, and the filtrate was washed twice with brine. The organic layer was dried over Na2SO4 and concentrated under vacuum to furnish two products. After purification by column chromatography, 6a (Rf = 0.24 in 2:1 hexane: ether) was obtained as a colorless oil (32.5 mg, 42%), and 6b (Rf = 0.34 in 2:1 hexane: ether) was obtained as a colorless oil (17.5 mg, 20 %). 6a: 1H NMR (400 MHz, CDCl3) δ 8.76 (d, J = 4.8 Hz, IH), 7.81 (td, J = 7.6, 1.6 Hz, IH), 7.74 (d, J= 10.2 Hz, 2H), 7.68 (d, J= 8.0 Hz, IH), 7.62 (d, J= 8.0 Hz, IH)5 7.35 (td, J = 7.6, 1.6 Hz, IH); 13C NMR (100 MHz, CDCl3) δ 155.85, 150.13, 142.83, 136.42, 133.13, 132.47, 128.49, 127.55 (d, J = 3.8 Hz), 125.16, 124.15 (d, J = 3.8 Hz), 123.42; IR (thin film) v 1325, 1130 cm"1; HRMS (TOF) Calcd for C12H8ClF3N (M + H) 258.0297, found 258.0284.6b: 1H NMR (400 MHz, CDCl3) δ 8.78 (d, J= 4.8 Hz, IH), 7.86 (td, J= 7.6, 1.6 Hz, IH), 7.69 (s, 2H), 7.41-7.38 (m, IH), 7.34 (d, J = 6.8 Hz, IH); 13C NMR (100 MHz, CDCl3) δ 154.70, 150.28, 142.11, 136.99, 135.95, 132.68 (q, J= 33.4 Hz), 127.53, 125.54 (q, J= 3.7 Hz), 125.05, .124.23, 123.81; IR (thin film) v 2924, 1385, 1317 cnT1; HRMS (TOF) Calcd for Ci2H7Cl2F3N (M + H) 291.9908, found 291.9896.

Reference： [1]Mo, Song; Zhu, Yamin; Shen, Zengming [Organic and Biomolecular Chemistry, 2013, vol. 11, # 17, p. 2756 - 2760]
[2]Lu, Yongzhong; Wang, Ruiping; Qiao, Xixue; Shen, Zengming [Synlett, 2011, # 7, p. 1038 - 1042]
[3]Chen, Xiao; Hao, Xue-Shi; Goodhue, Charles E.; Yu, Jin-Quan [Journal of the American Chemical Society, 2006, vol. 128, # 21, p. 6790 - 6791]
[4]Current Patent Assignee: BRANDEIS UNIVERSITY - WO2007/123910, 2007, A2 Location in patent: Page/Page column 29; 46

4
[ 823-96-1 ]
[ 203065-88-7 ]
2-(2-methyl-4-(trifluoromethyl)phenyl)pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
50%	With copper diacetate; air; p-benzoquinone In dichloromethane at 100℃; for 24h;

Reference： [1]Chen, Xiao; Goodhue, Charles E.; Yu, Jin-Quan [Journal of the American Chemical Society, 2006, vol. 128, # 39, p. 12634 - 12635]

5
[ 455-13-0 ]
[ 13737-04-7 ]
[ 203065-88-7 ]

Reference： [1]Tetrahedron Letters,2008,vol. 49,p. 6314 - 6315

6
[ 536-74-3 ]
[ 203065-88-7 ]
[ 1085411-81-9 ]

Yield	Reaction Conditions	Operation in experiment
98%	With silver hexafluoroantimonate; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer In acetic acid at 20℃; for 12h; Schlenk technique; Inert atmosphere;	GENERAL PROCEDURE: General procedure: To a dried Schlenk tube was equipped with a magnetic stirbar. [Cp*RhCl2]2 (0.005 mmol, 2.5 mol %, 3.1 mg), AgSbF6 (0.03 mmol, 15 mol %,10.3 mg), substrate 1 (0.2 mmol or 0.4 mmol), HOAc (1 ml), substrate 2 (0.24 mmolor 0.2 mmol) were added sequentially under argon. The tube was stirred at roomtemperature or 80 °C for 12 h. After completion of the reaction, the mixture wasdiluted with EtOAc (10 mL), filtered through a short pad of silica gel and washedwith EtOAc (30 mL). The filtrate was pre-absorbed on silica gel and concentrated byrotary evaporation. The crude product was purified by flash silica gel (300-400 mesh)chromatography to afford the desired products product 3.
70%	With 1-methyl-pyrrolidin-2-one; ruthenium trichloride; potassium carbonate; dibenzoyl peroxide at 150℃; for 6h; stereoselective reaction;

Reference： [1]Duan, Chang-Lin; Liu, Xing-Yu; Tan, Yun-Xuan; Ding, Rui; Yang, Shiping; Tian, Ping; Lin, Guo-Qiang [Synlett, 2019, vol. 30, # 8, p. 932 - 938]
[2]Cheng, Kai; Yao, Bangben; Zhao, Jinlong; Zhang, Yuhong [Organic Letters, 2008, vol. 10, # 22, p. 5309 - 5312]

7
[ 71-41-0 ]
[ 201230-82-2 ]
[ 203065-88-7 ]
[ 1101187-19-2 ]

Yield	Reaction Conditions	Operation in experiment
80%	With chloro(1,5-cyclooctadiene)rhodium(I) dimer; oxone In toluene at 110℃; for 8h; Autoclave;

Reference： [1]Guan, Zheng-Hui; Ren, Zhi-Hui; Liang, Yong-Min; Spinella, Stephen M.; Yu, Shichao; Zhang, Xumu [Journal of the American Chemical Society, 2009, vol. 131, # 2, p. 729 - 733]

8
[ 109-04-6 ]
[ 128796-39-4 ]
[ 203065-88-7 ]

Yield	Reaction Conditions	Operation in experiment
99%	With [(t-Bu)3PH]BF₄; palladium diacetate; sodium hydroxide at 20℃; for 0.25h; Inert atmosphere; Glovebox;
96.5%	With tetrakis-(triphenylphosphine)-palladium; anhydrous sodium carbonate In ethanol; toluene for 24h; Reflux; Inert atmosphere;	General Synthesis of 2-Phenylpyridine Derivatives. General procedure: In250 mL round bottom flask, 20 mmol 2-bromopyridinewas mixed with 24 mmol phenylboric acid (N: N = 1:1.2), and 0.6 mmol tetraphenylphosphine palladium (Pd(PPh3)4) was added as catalyst (Figure 2). A mixed solutionof 90 mL toluene, 30 mL anhydrous ethanol and30 mL sodium carbonate (2 mol/L) (V: V: V = 3:1:1)was heated to reflux for 24 h under nitrogen. Aftercooling to room temperature, the reaction mixture wasfiltered off solid. Separated organic layer, and the aqueousphase was extracted with CH2Cl2 (30 mL × 3), combinedorganic phases and washed with saturated NaClsolution. The washed organic phase was dried out byadding with an appropriate amount of anhydrous Na2SO4for 5 h. The solvent was removed by filtration underreduced pressure and the residue was purified by columnchromatography (petroleum:ethyl acetate = 20:1) to givethe pure product.
92%	With tripotassium phosphate tribasic; palladium diacetate; triphenylphosphine In propyl alcohol; lithium hydroxide monohydrate at 20℃; Reflux;

85%	With tetrakis-(triphenylphosphine)-palladium; potassium carbonate In tetrahydrofuran; lithium hydroxide monohydrate at 70℃; for 24h; Inert atmosphere;
84.5%	With palladium diacetate; potassium carbonate In ethanol; lithium hydroxide monohydrate at 80℃;
84.6%	With palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride; potassium carbonate at 90℃; for 12h; Inert atmosphere;
82%	With palladium diacetate; potassium carbonate; triphenylphosphine In methanol; acetonitrile at 65℃; for 24h; Inert atmosphere;	2. General procedure for the Suzuki cross-coupling of N-hetero-aryl halides with arylboronic acids. General procedure: Method B: The preparation of 2-Bromopyridines with arylboronic acids was according to literature procedures.[1] To a 50-mL fire-dried flask was charged with 2-Bromopyridines (5 mmol, 1.0 eq), arylboronic acid (5.5 mmol, 1.5 eq), K2CO3 (1.38 g, 10.0 mmol, 2.0 eq), Pd(OAc)2 (56.0 mg, 0.25 mmol, 5.0 mol% ), PPh3 (131.0 mg, 0.5 mmol, 10.0 mol% ), CH3CN (10.0 mL) and methanol (5.0 mL). The mixture was degassed through a freeze-thaw-pump thread for three times. The reaction was stirred at 65 °C for 24 hours. To the reaction mixture was added brine (15 mL) and ethyl acetate (15 mL). The phase was separated and the aqueous phase was extracted with ethyl acetate (4 × 15 mL). The combined organic phase was dried over Na2SO4 and concentrated under vacuum. The product was isolated by flash-column chromatography on silica gel (300-400 mesh).
79%	With tripotassium phosphate tribasic In ethanol; lithium hydroxide monohydrate at 100℃; for 8h;	2.4. General procedure for Suzuki coupling reaction catalyzed bypolymer anchored-Pd(II) D General procedure: A dried round bottomed flask equipped with a magnetic stirring bar was charged with 10mg Polymer anchored-Pd(II) D catalyst (PS-NPPZ-Pd) (0.0045mmol/Pd), 2-halopyridine (0.5mmol), phenylboronic acid (0.6mmol) and K3PO4 (1.0mmol) were added to a reaction vessel. The mixture was stirred in 4mL of H2O: EtOH (1:1) at 100°C for 8h and then cooled to room temperature. The catalyst was filtered and the filtrate was extracted with ethyl acetate (3×10mL). The combined organic layers were extracted with water, and dried over anhydrous Na2SO4. The organic layers were evaporated under reduced pressure and the resulting crude product was purified by column chromatography by using ethyl acetate/hexane (10:90) as eluent to give the corresponding coupled products. The products were characterized by 1H NMR, 13C NMR and HRMS analysis.
78%	With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); anhydrous sodium carbonate In 1,4-dioxane; lithium hydroxide monohydrate at 120℃; Inert atmosphere;
78%	With tetrakis-(triphenylphosphine)-palladium; potassium carbonate In ethanol; lithium hydroxide monohydrate; toluene for 24h; Inert atmosphere; Reflux;
76%	With tetrakis-(triphenylphosphine)-palladium; anhydrous sodium carbonate In tetrahydrofuran; lithium hydroxide monohydrate at 70℃; for 24h;
76%	With tetrakis-(triphenylphosphine)-palladium; anhydrous sodium carbonate In tetrahydrofuran; lithium hydroxide monohydrate at 70℃; for 24h;	2.3.1. General synthesis of L2-L4 General procedure: Tetraphenylimidodiphosphinate acid (Htpip) and potassiumtetraphenylimidodiphosphinate (Ktpip) were prepared accordingto our previous literatures [41-44]. All CF3-substituted ligandsL2L4 with a ppy core were synthesized by the reaction of thecorresponding 2-bromopyridine (21.1 mmol) and arylboronic acids(25.5 mmol) using tetrakis(triphenylphosphine)-palladium(0)(0.63 mmol) as the catalyst in 50 mL of THF. After 30 mL of aqueous2NNa2CO3 was delivered, the reaction mixturewas heated at 70 °Cfor 1 day. The cooled mixture was poured into water and extractedwith CH2Cl2 (50 mL x 3). Finally, silica column purification (nhexane:EtOAc 10: 1 as the eluant) gave white solid products.
73%	With tetrakis-(triphenylphosphine)-palladium; potassium carbonate In tetrahydrofuran; lithium hydroxide monohydrate for 16h; Inert atmosphere; Reflux;
73%	With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); potassium carbonate In tetrahydrofuran; lithium hydroxide monohydrate at 80℃; for 14h; Inert atmosphere; Schlenk technique;
62%	With tetrakis-(triphenylphosphine)-palladium; potassium carbonate In ethanol at 100℃; for 15h; Inert atmosphere;
62%	With tetrakis-(triphenylphosphine)-palladium; potassium carbonate In ethanol at 100℃; for 15h; Inert atmosphere;
48%	With 1-butyl-3-methylimidazolium hexafluorophosphate; palladium diacetate; anhydrous sodium carbonate In lithium hydroxide monohydrate at 80℃; for 12h; Inert atmosphere;
45%	With tetrakis-(triphenylphosphine)-palladium; anhydrous sodium carbonate In tetrahydrofuran; lithium hydroxide monohydrate at 70℃; for 8h;
43%	With palladium diacetate; potassium carbonate; triphenylphosphine In lithium hydroxide monohydrate; N,N-dimethyl-formamide at 130℃; for 12h;
32%	With potassium phosphate heptahydrate; oxygen; palladium diacetate In isopropanol at 80℃;
	With tetrakis-(triphenylphosphine)-palladium; potassium carbonate In tetrahydrofuran; lithium hydroxide monohydrate at 85℃; Inert atmosphere;
	With tetrakis-(triphenylphosphine)-palladium; anhydrous sodium carbonate In ethanol; lithium hydroxide monohydrate; toluene for 12h; Inert atmosphere; Reflux;
	With tetrakis(triphenylphosphine)platinum⁽⁰⁾; potassium carbonate In tetrahydrofuran; lithium hydroxide monohydrate for 12h; Inert atmosphere; Reflux;
	With anhydrous sodium carbonate; triphenylphosphine
	With palladium diacetate
	With tetrakis-(triphenylphosphine)-palladium; anhydrous sodium carbonate In ethanol; lithium hydroxide monohydrate; toluene for 12h; Reflux;
	With tetrakis-(triphenylphosphine)-palladium; anhydrous sodium carbonate In ethanol; lithium hydroxide monohydrate; toluene at 12℃; Inert atmosphere; Resolution of racemate;
	With tetrakis-(triphenylphosphine)-palladium; anhydrous sodium carbonate In ethanol; lithium hydroxide monohydrate; toluene at 95℃; for 18h;
	With tetrakis-(triphenylphosphine)-palladium; anhydrous sodium carbonate In ethanol; lithium hydroxide monohydrate; toluene for 16h; Inert atmosphere; Schlenk technique; Reflux;
	With palladium diacetate; potassium carbonate; triphenylphosphine In lithium hydroxide monohydrate; N,N-dimethyl-formamide at 130℃; for 12h;
	With potassium phosphate heptahydrate In lithium hydroxide monohydrate; isopropanol at 80℃; for 3h;
	With tetrakis-(triphenylphosphine)-palladium; anhydrous sodium carbonate In ethanol; lithium hydroxide monohydrate; toluene for 12h; Inert atmosphere; Reflux;
	With palladium diacetate; potassium carbonate In ethanol; lithium hydroxide monohydrate at 80℃; for 1h;	12.1 Synthesis of Compound 12 Ligand synthesis: In air,To a round bottom flask was added 4-trifluoromethylbenzeneboronic acid (0.375 mmol) in that order,Potassium carbonate (0.5 mmo 1),Palladium acetate (0.005 mmol),2-Bromopyridine (0.25 mmo1),then,An ethanol-water mixed solution (4 mL) in a volume ratio of 3: 1 was added,The Suzuki cross-coupling reaction was carried out at 80 ° C for 60 minutes with magnetic stirring,After completion of the reaction,Saturated brine (15 mL) was added,The reaction product was extracted with ethyl acetate (3 X 15 ml)The organic phases were combined,The filtrate was concentrated,After separation by column chromatography,To yield analytically pure 2- (4-trifluoromethylphenyl) pyridine.
	With tetrakis-(triphenylphosphine)-palladium
	With tetrakis-(triphenylphosphine)-palladium; anhydrous sodium carbonate In ethanol; lithium hydroxide monohydrate; toluene for 12h; Reflux; Inert atmosphere;
	With tetrakis-(triphenylphosphine)-palladium; anhydrous sodium carbonate In ethanol; lithium hydroxide monohydrate; toluene at 120℃; for 12h; Inert atmosphere; Schlenk technique;
	With tetrakis-(triphenylphosphine)-palladium; potassium carbonate In tetrahydrofuran; lithium hydroxide monohydrate at 75℃; for 12h; Inert atmosphere;
	With tetrakis-(triphenylphosphine)-palladium; anhydrous sodium carbonate In ethanol; lithium hydroxide monohydrate; toluene for 12h; Inert atmosphere; Schlenk technique; Reflux;
	With tetrakis-(triphenylphosphine)-palladium; anhydrous sodium carbonate at 80℃; for 10h;
	With potassium phosphate heptahydrate; palladium diacetate In ethylene glycol at 80℃; for 24h; Inert atmosphere;
	With tetrakis-(triphenylphosphine)-palladium; potassium carbonate In ethanol; lithium hydroxide monohydrate; toluene at 75℃; for 24h; Inert atmosphere;
	With tetrakis-(triphenylphosphine)-palladium; potassium carbonate In ethanol; lithium hydroxide monohydrate; toluene at 100℃; for 18h; Inert atmosphere;

Reference： [1]Zou, Yinjun; Yue, Guizhou; Xu, Jianwei; Zhou, Jianrong [European Journal of Organic Chemistry, 2014, vol. 2014, # 27, p. 5901 - 5905]
[2]Guo, Qing-Mei; Huang, Guo-Li; Yin, Xin-Ying; Bian, Jian-Jian; Li, Xiao-Mei; Teng, Ming-Yu [Bulletin of the Korean Chemical Society, 2020, vol. 41, # 12, p. 1184 - 1189]
[3]Hylland, Knut T.; Nova, Ainara; Schmidtke, Inga L.; Tilset, Mats; Wragg, David S. [Dalton Transactions, 2022, vol. 51, # 13, p. 5082 - 5097]
[4]Lu, Guang-Zhao; Jing, Yi-Ming; Han, Hua-Bo; Fang, Yu-Liang; Zheng, You-Xuan [Organometallics, 2017, vol. 36, # 2, p. 448 - 454]
[5]Liu, Chun; Lv, Xin; Xing, Yang; Qiu, Jieshan [Journal of Materials Chemistry C, 2015, vol. 3, # 31, p. 8010 - 8017]
[6]Yang, Xiao-Han; Li, Min; Peng, Hui; Zhang, Qian; Wu, Shui-Xing; Xiao, Wan-Qing; Chen, Xing-Liang; Niu, Zhi-Gang; Chen, Guang-Ying; Li, Gao-Nan [European Journal of Inorganic Chemistry, 2019, vol. 2019, # 6, p. 847 - 855]
[7]Zhong, Lei; Zong, Zhi-Hong; Wang, Xi-Cun [Tetrahedron, 2019, vol. 75, # 17, p. 2547 - 2552]
[8]Perumgani, Pullaiah C.; Kodicherla, Balaswamy; Mandapati, Mohan Rao; Parvathaneni, Sai Prathima [Inorganica Chimica Acta, 2018, vol. 477, p. 227 - 232]
[9]Wübbolt, Simon; Oestreich, Martin [Angewandte Chemie - International Edition, 2015, vol. 54, # 52, p. 15876 - 15879][Angew. Chem., 2015, vol. 127, # 52, p. 16103 - 16106,4]
[10]Su, Ning; Lu, Guang-Zhao; Zheng, You-Xuan [Journal of Materials Chemistry C, 2018, vol. 6, # 21, p. 5778 - 5784]
[11]Xu, Qiu-Lei; Wang, Cheng-Cheng; Li, Tian-Yi; Teng, Ming-Yu; Zhang, Song; Jing, Yi-Ming; Yang, Xu; Li, Wei-Nan; Lin, Chen; Zheng, You-Xuan; Zuo, Jing-Lin; You, Xiao-Zeng [Inorganic Chemistry, 2013, vol. 52, # 9, p. 4916 - 4925]
[12]Lu, Guang-Zhao; Han, Hua-Bo; Li, Yan; Zheng, You-Xuan [Dyes and Pigments, 2017, vol. 143, p. 33 - 41]
[13]Chen, Shuonan; Gai, Xi; Liang, Jie; Liu, Yu; Wang, Yue; Ye, Kaiqi [Journal of Materials Chemistry C, 2021, vol. 9, # 26, p. 8329 - 8336]
[14]Martín, Jaime; Gómez-Bengoa, Enrique; Genoux, Alexandre; Nevado, Cristina [Angewandte Chemie - International Edition, 2022, vol. 61, # 20][Angew. Chem., 2022, vol. 134, # 20]
[15]Paterson, Andrew J.; St John-Campbell, Sahra; Mahon, Mary F.; Press, Neil J.; Frost, Christopher G. [Chemical Communications, 2015, vol. 51, # 64, p. 12807 - 12810]
[16]Paterson, Andrew J.; Heron, Callum J.; McMullin, Claire L.; Mahon, Mary F.; Press, Neil J.; Frost, Christopher G. [Organic and Biomolecular Chemistry, 2017, vol. 15, # 28, p. 5993 - 6000]
[17]Location in patent: experimental part Xin, Bingwei [Journal of Chemical Research, 2008, # 7, p. 412 - 415]
[18]Funaki, Takashi; Otsuka, Hiromi; Onozawa-Komatsuzaki, Nobuko; Kasuga, Kazuyuki; Sayama, Kazuhiro; Sugihara, Hideki [Journal of Materials Chemistry A, 2014, vol. 2, # 38, p. 15945 - 15951]
[19]Wang, Xiaoling; Ji, Xiaoming; Shao, Changdong; Zhang, Yu; Zhang, Yanghui [Organic and Biomolecular Chemistry, 2017, vol. 15, # 26, p. 5616 - 5624]
[20]Mo, Song; Zhu, Yamin; Shen, Zengming [Organic and Biomolecular Chemistry, 2013, vol. 11, # 17, p. 2756 - 2760]
[21]Shavaleev, Nail M.; Monti, Filippo; Scopelliti, Rosario; Armaroli, Nicola; Graetzel, Michael; Nazeeruddin, Mohammad K. [Organometallics, 2012, vol. 31, # 17, p. 6288 - 6296]
[22]Reddy, Vutukuri Prakash; Qiu, Renhua; Iwasaki, Takanori; Kambe, Nobuaki [Organic Letters, 2013, vol. 15, # 6, p. 1290 - 1293]
[23]Feng, Chen-Guo; Ye, Mengchun; Xiao, Kai-Jiong; Li, Suhua; Yu, Jin-Quan [Journal of the American Chemical Society, 2013, vol. 135, # 25, p. 9322 - 9325]
[24]Li, Tian-Yi; Liang, Xiao; Wu, Chen; Xue, Li-Sha; Xu, Qiu-Lei; Zhang, Song; Liu, Xuan; Zheng, You-Xuan; Wang, Xiu-Qiang [Journal of Organometallic Chemistry, 2014, vol. 755, p. 110 - 119]
[25]Li, Hong-Yan; Li, Tian-Yi; Teng, Ming-Yu; Xu, Qiu-Lei; Zhang, Song; Jin, Yi-Ming; Liu, Xuan; Zheng, You-Xuan; Zuo, Jing-Lin [Journal of Materials Chemistry C, 2014, vol. 2, # 6, p. 1116 - 1124]
[26]Xu, Hui; Qiao, Xixue; Yang, Shiping; Shen, Zengming [Journal of Organic Chemistry, 2014, vol. 79, # 10, p. 4414 - 4422]
[27]Cai, Jian-Guang; Yu, Zhen-Tao; Yuan, Yong-Jun; Li, Feng; Zou, Zhi-Gang [ACS Catalysis, 2014, vol. 4, # 6, p. 1953 - 1963]
[28]Patel, Pitambar; Chang, Sukbok [Organic Letters, 2014, vol. 16, # 12, p. 3328 - 3331]
[29]Kim, Hyunwoo; Park, Juhyeon; Kim, Jeung Gon; Chang, Sukbok [Organic Letters, 2014, vol. 16, # 20, p. 5466 - 5469]
[30]Pawar, Amit B.; Chang, Sukbok [Organic Letters, 2015, vol. 17, # 3, p. 660 - 663]
[31]Zhao, Dongbing; Kim, Ju Hyun; Stegemann, Linda; Strassert, Cristian A.; Glorius, Frank [Angewandte Chemie - International Edition, 2015, vol. 54, # 15, p. 4508 - 4511][Angew. Chem., 2015, vol. 127, # 15, p. 4591 - 4594,4] Kim, Ju Hyun; Gensch, Tobias; Zhao, Dongbing; Stegemann, Linda; Strassert, Cristian A.; Glorius, Frank [Angewandte Chemie - International Edition, 2015, vol. 54, # 37, p. 10975 - 10979][Angew. Chem., 2015, vol. 127, # 37, p. 11126 - 11130,5]
[32]Premi, Chanchal; Dixit, Ankit; Jain, Nidhi [Organic Letters, 2015, vol. 17, # 11, p. 2598 - 2601]
[33]Kishore, Ramineni; Yadav, Jagjit; Venu, Boosa; Venugopal, Akula; Lakshmi Kantam [New Journal of Chemistry, 2015, vol. 39, # 7, p. 5259 - 5264]
[34]Kim, Jiyu; Park, Sung-Woo; Baik, Mu-Hyun; Chang, Sukbok [Journal of the American Chemical Society, 2015, vol. 137, # 42, p. 13448 - 13451]
[35]Current Patent Assignee: DALIAN UNIVERSITY OF TECHNOLOGY - CN103145763, 2016, B Location in patent: Paragraph 0078
[36]Lu, Guang-Zhao; Li, Yan; Jing, Yi-Ming; Zheng, You-Xuan [Dalton Transactions, 2017, vol. 46, # 1, p. 150 - 157]
[37]Zhang, Guo-Fu; Li, Yue; Xie, Xiao-Qiang; Ding, Cheng-Rong [Organic Letters, 2017, vol. 19, # 5, p. 1216 - 1219]
[38]Qi, Chaorong; Hu, Xiaohan; Jiang, Huanfeng [Chemical Communications, 2017, vol. 53, # 57, p. 7994 - 7997]
[39]Thongpaen, Jompol; Schmid, Thibault E.; Toupet, Loic; Dorcet, Vincent; Mauduit, Marc; Baslé, Olivier [Chemical Communications, 2018, vol. 54, # 59, p. 8202 - 8205]
[40]Xia, Jing-Cheng; Liang, Xiao; Yan, Zhi-Ping; Wu, Zheng-Guang; Zhao, Yue; Zheng, You-Xuan; Zhang, Wen-Wei [Journal of Materials Chemistry C, 2018, vol. 6, # 33, p. 9010 - 9016]
[41]Li, Zhong-Yuan; Chaminda Lakmal, Hetti Handi; Cui, Xin [Organic Letters, 2019, vol. 21, # 10, p. 3735 - 3740]
[42]Zhang, Lin; Yan, Zhi-Ping; Tu, Zhen-Long; Wu, Zheng-Guang; Zheng, You-Xuan [Journal of Materials Chemistry C, 2019, vol. 7, # 37, p. 11606 - 11611]
[43]Li, Gang; Gao, Yuan; Jia, Chunqi; Wang, Shichong; Yan, Bingxu; Fang, Yu; Yang, Suling [Organic Letters, 2020, vol. 22, # 22, p. 8758 - 8763]
[44]Clarke, Joshua J.; Maekawa, Yuuki; Nambo, Masakazu; Crudden, Cathleen M. [Organic Letters, 2021, vol. 23, # 17, p. 6617 - 6621]
[45]Li, Jiangang; Chen, Kexin; Wei, Juan; Ma, Yun; Zhou, Ruyi; Liu, Shujuan; Zhao, Qiang; Wong, Wai-Yeung [Journal of the American Chemical Society, 2021, vol. 143, # 43, p. 18317 - 18324]
[46]Yang, Qi-Liang; Liu, Ying; Liang, Lei; Li, Zhi-Hao; Qu, Gui-Rong; Guo, Hai-Ming [Journal of Organic Chemistry, 2022, vol. 87, # 9, p. 6161 - 6178]
[47]Cui, Xiuling; Jia, Chunqi; Li, Gang; Wu, Nini [Journal of Organic Chemistry, 2022]

9
[ 203065-88-7 ]
[ 1151554-19-6 ]

Yield	Reaction Conditions	Operation in experiment
65%	With sulfuric acid; iodine; palladium diacetate In water; acetonitrile at 90℃; for 4h; Electrochemical reaction; regioselective reaction;
58%	With iodine; copper diacetate In acetonitrile at 130℃; for 24h; sealed tube; regioselective reaction;

Reference： [1]Saito, Fumito; Aiso, Hiroko; Kochi, Takuya; Kakiuchi, Fumitoshi [Organometallics, 2014, vol. 33, # 22, p. 6704 - 6707]
[2]Location in patent: experimental part Chen, Xiao; Dobereiner, Graham; Hao, Xue-Shi; Giri, Ramesh; Maugel, Nathan; Yu, Jin-Quan [Tetrahedron, 2009, vol. 65, # 16, p. 3085 - 3089]

10
[ 541-41-3 ]
[ 203065-88-7 ]
[ 1128193-21-4 ]
[ 1128193-23-6 ]

Yield	Reaction Conditions	Operation in experiment
1: 47% 2: 8%	With tris(triphenylphosphine)ruthenium(II) chloride; potassium carbonate In toluene at 120℃; for 12h;

Reference： [1]Kochi, Takuya; Urano, Seiya; Seki, Hajime; Mizushima, Eiichiro; Sato, Mitsuo; Kakiuchi, Fumitoshi [Journal of the American Chemical Society, 2009, vol. 131, p. 2792 - 2793]

11
[ 455-13-0 ]
[ 21970-13-8 ]
[ 203065-88-7 ]

Yield	Reaction Conditions	Operation in experiment
91%	With C₄₂H₆₄O₄P₂Pd In tetrahydrofuran at 60℃; for 20h; Inert atmosphere; chemoselective reaction;

Reference： [1]Ackermann, Lutz; Potukuchi, Harish K.; Kapdi, Anant R.; Schulzke, Carola [Chemistry - A European Journal, 2010, vol. 16, # 11, p. 3300 - 3303]

12
[ 402-43-7 ]
[ 21970-13-8 ]
[ 203065-88-7 ]

Yield	Reaction Conditions	Operation in experiment
86%	With C₄₂H₆₄O₄P₂Pd In tetrahydrofuran at 60℃; for 20h; Inert atmosphere; chemoselective reaction;

Reference： [1]Ackermann, Lutz; Potukuchi, Harish K.; Kapdi, Anant R.; Schulzke, Carola [Chemistry - A European Journal, 2010, vol. 16, # 11, p. 3300 - 3303]

13
[ 611-73-4 ]
[ 203065-88-7 ]
[ 1236046-63-1 ]

Yield	Reaction Conditions	Operation in experiment
56%	With dipotassium peroxodisulfate; bis(benzonitrile)palladium(II) dichloride; silver(l) oxide In 1,4-dioxane; acetic acid; dimethyl sulfoxide at 120℃; for 16h;

Reference： [1]Li, Mingzong; Ge, Haibo [Organic Letters, 2010, vol. 12, # 15, p. 3464 - 3467]

14
[ 623-12-1 ]
[ 203065-88-7 ]
[ 1251668-10-6 ]

Yield	Reaction Conditions	Operation in experiment
80%	With [Ru(MesCO₂)₂(p-cymene)]; potassium carbonate In toluene at 120℃; for 18h; Inert atmosphere;
73%	With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; N,N-bis-(mesityl)imidazolium chloride; cyclohexylmagnesiumchloride; cobalt(II) aceylacetonate at 23℃; for 16h; Inert atmosphere;

Reference： [1]Ackermann, Lutz; Vicente, Ruben; Potukuchi, Harish K.; Pirovano, Valentina [Organic Letters, 2010, vol. 12, # 21, p. 5032 - 5035]
[2]Punji, Benudhar; Song, Weifeng; Shevchenko, Grigory A.; Ackermann, Lutz [Chemistry - A European Journal, 2013, vol. 19, # 32, p. 10605 - 10610]

15
[ 98-56-6 ]
pyridin-2-ylzinc(II) bromide [ No CAS ]
[ 203065-88-7 ]

Yield	Reaction Conditions	Operation in experiment
86%	With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; XPhos In tetrahydrofuran at 65℃; for 2.5h; Inert atmosphere;

Reference： [1]Luzung, Michael R.; Patel, Jigar S.; Yin, Jingjun [Journal of Organic Chemistry, 2010, vol. 75, # 23, p. 8330 - 8332]

16
[ 109-04-6 ]
[ 402-43-7 ]
[ 203065-88-7 ]

Yield	Reaction Conditions	Operation in experiment
86%	Stage #1: p-trifluoromethylphenyl bromide With ethylene dibromide; trifluoroacetic acid; cobalt(II) bromide; zinc In acetonitrile at 20℃; for 1h; Inert atmosphere; Sealed tube; Stage #2: 2-bromo-pyridine With bis-triphenylphosphine-palladium(II) chloride In N,N-dimethyl-formamide; acetonitrile at 50℃; for 1h; Inert atmosphere; Sealed tube;
76%	With manganese; nickel bromide 2,2’-bipyridine complex; trifluoroacetic acid In N,N-dimethyl-formamide at 20℃; for 1h;

Reference： [1]Xavier, Tania; Rayapin, Corinne; Le Gall, Erwan; Presset, Marc [Chemistry - A European Journal, 2019, vol. 25, # 60, p. 13824 - 13828]
[2]Location in patent: experimental part Gosmini, Corinne; Bassene-Ernst, Carine; Durandetti, Muriel [Tetrahedron, 2009, vol. 65, # 31, p. 6141 - 6146]

17
[ 203065-88-7 ]
[ 100-51-6 ]
[ 1236046-63-1 ]

Yield	Reaction Conditions	Operation in experiment
78%	With tert-Butyl peroxybenzoate In chlorobenzene at 130℃; for 18h; Sealed tube;
72%	With tert.-butylhydroperoxide; chlorobenzene; palladium dichloride In water at 140℃; for 24h; Sealed tube; regioselective reaction;
60%	With tert.-butylhydroperoxide In water; chlorobenzene at 120℃; for 8h;	General procedure for the oxidative sp² C-H bond acylation with alcohols General procedure: In a typical reaction, a 10 mL oven-dried reaction vessel was charged with Pd/MgLa mixed oxide (30 mg), 2-phenylpyridine (29 mg, 0.2 mmol), benzyl alcohol (108 mg, 1 mmol), tert-butyl hydroperoxide (70% solution in water, ∼129 mg, 1 mmol) and chlorobenzene (0.5 mL) were added. The resulting solution was stirred at 120 °C for 8 h in open air. The reaction was monitored by thin-layer chromatography (TLC). After cooling to room temperature, catalyst was separated by simple centrifugation. The filtrate was concentrated under reduced pressure and the residue was purified by column chromatography using silica gel and a mixture of hexane/ethyl acetate as eluents. All the products were confirmed by 1H NMR and 13C NMR spectroscopy. The recovered catalyst was used for the next cycle without any further purification.

Reference： [1]Huang, Fei; Wang, Feifan; Hu, Qiyan; Tang, Lin; Xu, Dongping; Fang, Yang; Zhang, Wu [Applied Organometallic Chemistry, 2021, vol. 35, # 7]
[2]Xiao, Fuhong; Shuai, Qi; Zhao, Feng; Basle, Olivier; Deng, Guojun; Li, Chao-Jun [Organic Letters, 2011, vol. 13, # 7, p. 1614 - 1617]
[3]Kishore; Kantam, M. Lakshmi; Yadav; Sudhakar; Laha; Venugopal [Journal of Molecular Catalysis A: Chemical, 2013, vol. 379, p. 213 - 218]

18
[ 107607-16-9 ]
[ 203065-88-7 ]
[ 1128193-21-4 ]

Yield	Reaction Conditions	Operation in experiment
54%	With palladium dichloride In chloroform at 100℃; for 24h; Inert atmosphere; Sealed tube;

Reference： [1]Peng, Xingao; Zhu, Yingguang; Ramirez, Thomas A.; Zhao, Baoguo; Shi, Yian [Organic Letters, 2011, vol. 13, # 19, p. 5244 - 5247]

19
[ 203065-88-7 ]
[ 158461-30-4 ]

Yield	Reaction Conditions	Operation in experiment
70%	With tert.-butylnitrite; oxygen; palladium diacetate In chlorobenzene at 100℃; for 24h; regioselective reaction;
43%	With oxygen; copper diacetate; silver nitrate In 1,2,3-trichloropropane at 130℃; for 60h; regioselective reaction;

Reference： [1]Liang, Yu-Feng; Li, Xinyao; Wang, Xiaoyang; Yan, Yuepeng; Feng, Peng; Jiao, Ning [ACS Catalysis, 2015, vol. 5, # 3, p. 1956 - 1963]
[2]Zhang, Lin; Liu, Zhenhua; Li, Huiqin; Fang, Guichun; Barry, Badru-Deen; Belay, Tuemay Abadi; Bi, Xihe; Liu, Qun [Organic Letters, 2011, vol. 13, # 24, p. 6536 - 6539]

20
[ 33675-27-3 ]
[ 125102-17-2 ]
[ 203065-88-7 ]

Yield	Reaction Conditions	Operation in experiment
82%	With C₃₂H₂₆ClN₂NiP In tetrahydrofuran; 1-methyl-pyrrolidin-2-one at 85℃; for 12h; Inert atmosphere;

Reference： [1]Location in patent: experimental part Zhang, Xue-Qi; Wang, Zhong-Xia [Journal of Organic Chemistry, 2012, vol. 77, # 7, p. 3658 - 3663]

21
[ 110-86-1 ]
[ 455-13-0 ]
[ 203065-88-7 ]
[ 220000-88-4 ]
[ 426823-25-8 ]

Reference： [1]Chemical Communications,2012,vol. 48,p. 6702 - 6704
[2]Organic and Biomolecular Chemistry,2022,vol. 20,p. 208 - 218

22
[ 941-55-9 ]
[ 203065-88-7 ]
[ 1379667-23-8 ]

Yield	Reaction Conditions	Operation in experiment
93%	With bromopentacarbonylmanganese(I); tetrabutylammomium bromide In water at 120℃; for 16h; regioselective reaction;
82%	With silver hexafluoroantimonate; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer In 1,2-dichloro-ethane at 80℃; for 24h; Inert atmosphere;
82%	With RuHCl(CO)(PPh<SUB>3</SUB>)<SUB>3</SUB> In 1,2-dichloro-ethane at 100℃; for 12h; Sealed tube; Inert atmosphere;

80%	With silver hexafluoroantimonate; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer In 1,2-dichloro-ethane at 80℃; for 12h;
64%	With silver hexafluoroantimonate; [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂; sodium acetate In 1,2-dichloro-ethane at 80℃; for 12h;
38%	With C₂₂H₂₈Cl₂InNRh⁽¹⁺⁾*C₃₂H₁₂BF₂₄^(1-) In toluene at 120℃; for 4h; Inert atmosphere;
31%	With copper(I) thiophene-2-carboxylate; Trimethylacetic acid In 1,2-dichloro-benzene at 110℃; for 36h; Inert atmosphere; Sealed tube;

Reference： [1]Kong, Xianqiang; Lin, Long; Xu, Bo [Advanced Synthesis and Catalysis, 2018, vol. 360, # 15, p. 2801 - 2805]
[2]Park, Sae Hume; Park, Yoonsu; Chang, Sukbok [Organic Syntheses, 2014, vol. 91, p. 52 - 59]
[3]Xiao, Xinsheng; Jia, Guokai; Liu, Fang; Ou, Guangchuan; Xie, Ying [Journal of Organic Chemistry, 2018, vol. 83, # 22, p. 13811 - 13820]
[4]Kim, Ji Young; Park, Sae Hume; Ryu, Jaeyune; Cho, Seung Hwan; Kim, Seok Hwan; Chang, Sukbok [Journal of the American Chemical Society, 2012, vol. 134, # 22, p. 9110 - 9113]
[5]Kim, Jiyu; Kim, Jinwoo; Chang, Sukbok [Chemistry - A European Journal, 2013, vol. 19, # 23, p. 7328 - 7333]
[6]Yamada, Ryosuke; Iwasawa, Nobuharu; Takaya, Jun [Angewandte Chemie - International Edition, 2019, vol. 58, # 48, p. 17251 - 17254][Angew. Chem., 2019, vol. 131, # 48, p. 17411 - 17414,4]
[7]Peng, Jiangling; Xie, Zeqiang; Chen, Ming; Wang, Jian; Zhu, Qiang [Organic Letters, 2014, vol. 16, # 18, p. 4702 - 4705]

23
iridium(III) chloride trihydrate [ No CAS ]
[ 203065-88-7 ]
[ 852358-23-7 ]

Yield	Reaction Conditions	Operation in experiment
84%	With 2-(2,4-difluorophenyl)pyridine In 2-methoxy-ethanol; water for 20h; Inert atmosphere; Reflux;
	In 2-ethoxy-ethanol; water at 120℃; Inert atmosphere;
	In 2-ethoxy-ethanol; water for 24h; Reflux;

	In 2-ethoxy-ethanol; water at 120℃; for 12h; Inert atmosphere;	2.4.2. General syntheses of iridium complexes Ir1-Ir7 IrCl3*3H2O (1.76 g, 5.0 mmol) and tfmppy (2.45 g, 11.0 mmol) in 6.0 mL 2-ethoxyethanol and 3.0 mL distilled water were heated at 120 °C for 12 h. After the solution was cooled, the addition of 30 mL water gave a bright yellow precipitate which was filtered and washed with distilled water and ethanol, yielding 3.09 g [(tfmppy)2Ir(m-Cl)]2 (2.30 mmol, 92.0%). The μ-chloro-bridged dimer complex was used for the subsequent reaction without characterization and further purification. [(tfmppy)2Ir(m-Cl)]2 (0.40 g, 0.30 mmol) and L1-L7 (0.65 mmol) in 5 mL 2-ethoxyethanol were heated at 120 °C. Potassium tert-butoxide(0.07 g, 0.65 mmol) in 5.0 mL MeOH was injected into the mixtures dropwise. After 12 h, the precipitates were filtered, washed with ethanol and gave the products as bright yellow powders. The pure complexes were obtained from recrystallization by using solvent diffusion of MeOH into CH2Cl2 solutions.
	In 2-ethoxy-ethanol; water for 24h; Reflux;
	In 2-ethoxy-ethanol; water at 110℃; for 12h;
	In 2-ethoxy-ethanol; water at 110℃; for 24h;
	In 2-ethoxy-ethanol; water Inert atmosphere;

Reference： [1]Chen, Shuonan; Gai, Xi; Liang, Jie; Liu, Yu; Wang, Yue; Ye, Kaiqi [Journal of Materials Chemistry C, 2021, vol. 9, # 26, p. 8329 - 8336]
[2]Shavaleev, Nail M.; Monti, Filippo; Scopelliti, Rosario; Armaroli, Nicola; Graetzel, Michael; Nazeeruddin, Mohammad K. [Organometallics, 2012, vol. 31, # 17, p. 6288 - 6296]
[3]Xu, Qiu-Lei; Wang, Cheng-Cheng; Li, Tian-Yi; Teng, Ming-Yu; Zhang, Song; Jing, Yi-Ming; Yang, Xu; Li, Wei-Nan; Lin, Chen; Zheng, You-Xuan; Zuo, Jing-Lin; You, Xiao-Zeng [Inorganic Chemistry, 2013, vol. 52, # 9, p. 4916 - 4925]
[4]Li, Tian-Yi; Liang, Xiao; Wu, Chen; Xue, Li-Sha; Xu, Qiu-Lei; Zhang, Song; Liu, Xuan; Zheng, You-Xuan; Wang, Xiu-Qiang [Journal of Organometallic Chemistry, 2014, vol. 755, p. 110 - 119]
[5]Li, Hong-Yan; Li, Tian-Yi; Teng, Ming-Yu; Xu, Qiu-Lei; Zhang, Song; Jin, Yi-Ming; Liu, Xuan; Zheng, You-Xuan; Zuo, Jing-Lin [Journal of Materials Chemistry C, 2014, vol. 2, # 6, p. 1116 - 1124]
[6]Li, Tian-Yi; Liang, Xiao; Zhou, Liang; Wu, Chen; Zhang, Song; Liu, Xuan; Lu, Guang-Zhao; Xue, Li-Sha; Zheng, You-Xuan; Zuo, Jing-Lin [Inorganic Chemistry, 2015, vol. 54, # 1, p. 161 - 173]
[7]Liu, Chun; Lv, Xin; Xing, Yang; Qiu, Jieshan [Journal of Materials Chemistry C, 2015, vol. 3, # 31, p. 8010 - 8017]
[8]Yang, Xiao-Han; Li, Min; Peng, Hui; Zhang, Qian; Wu, Shui-Xing; Xiao, Wan-Qing; Chen, Xing-Liang; Niu, Zhi-Gang; Chen, Guang-Ying; Li, Gao-Nan [European Journal of Inorganic Chemistry, 2019, vol. 2019, # 6, p. 847 - 855]

24
[ 766-47-2 ]
[ 203065-88-7 ]
[ 1421006-74-7 ]

Yield	Reaction Conditions	Operation in experiment
79%	With bromopentacarbonylmanganese(I); N-cyclohexyl-cyclohexanamine In diethyl ether at 80℃; for 6h; Inert atmosphere; Schlenk technique; stereoselective reaction;

Reference： [1]Zhou, Bingwei; Chen, Hui; Wang, Congyang [Journal of the American Chemical Society, 2013, vol. 135, # 4, p. 1264 - 1267]

25
[ 872-05-9 ]
[ 203065-88-7 ]
2-{2-n-decyl-4-(trifluoromethyl)phenyl}pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	With [RhCl₂(p-cymene)]2; potassium 2,4,6-trimethylbenzoate In toluene at 100℃; for 18h; Inert atmosphere; regioselective reaction;

Reference： [1]Schinkel, Marvin; Marek, Ilan; Ackermann, Lutz [Angewandte Chemie - International Edition, 2013, vol. 52, # 14, p. 3977 - 3980][Angew. Chem., 2013, vol. 125, # 14, p. 4069 - 4072,4]

26
[ 203065-88-7 ]
[ 1429027-50-8 ]

Yield	Reaction Conditions	Operation in experiment
85%	With tert.-butylhydroperoxide; palladium diacetate In water; 1,2-dichloro-ethane at 115℃; for 20h; Sealed tube;
77%	With oxone; Ru(MesCO<SUB>2</SUB>)(4,4'-dibromobipyridine)(p-cymene); trifluoroacetic acid; trifluoroacetic anhydride In 1,2-dichloro-ethane at 140℃; Sealed tube; Green chemistry; regioselective reaction;	General procedure for ruthenium-catalyzed ortho-hydroxylation of 2-arylpyridines General procedure: A mixture of 2-arylpyridines (1 eq), Ru(MesCO2)(L) (p-cymene) [L- 2,2’-bypyridine or 4,4’-dibromobipyridine] (5 mol%), TFA: TFAA=0.6 ml:0.4 ml and Oxone (4 eq) was taken in a 30 ml sealed tube. 1 ml of DCE was added and the tube was then placed in an oil bath, stirred, and heated at 140°C. The progress of the reaction was checked after every 8 hrs. After complete consumption of starting material the reaction mixture was cooled to room temperature, quenched with brine and extracted with dichloromethane. The combined organic layer was dried with anhydrous Na2SO4, and vacuum evaporated. The crude product was purified over a column of silica gel (eluent: hexane/ethyl acetate) to afford the desired products.
76%	With silver hexafluoroantimonate; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; [bis(acetoxy)iodo]benzene; water; acetic anhydride; acetic acid at 80℃; for 12h;

73%	With N-hydroxyphthalimide; oxygen; palladium dichloride In toluene at 100℃; for 15h; Schlenk technique;
62%	With dihydrogen peroxide; palladium dichloride In water at 100℃; for 24h;
	Multi-step reaction with 2 steps 1.1: C₂₈H₃₈ClN₂O₂Rh; sodium methylate / benzene / 0.17 h / Glovebox; Schlenk technique; Inert atmosphere 1.2: 16 h / 80 °C / Schlenk technique; Sealed tube; Inert atmosphere 2.1: Oxone / water; acetone
	Multi-step reaction with 2 steps 1: [RhCl₂(p-cymene)]2; sodium t-butanolate; C₃₃H₁₈F₆IrN₃⁽³⁺⁾ / tetrahydrofuran / 48 h / 20 °C / Sealed tube; Inert atmosphere; Irradiation 2: potassium peroxymonosulfate sulfate / acetone; water / 2 h / 20 °C / Inert atmosphere

Reference： [1]Dong, Jiawei; Liu, Ping; Sun, Peipei [Journal of Organic Chemistry, 2015, vol. 80, # 5, p. 2925 - 2929]
[2]Shome, Sanchari; Singh, Surya Prakash [Tetrahedron Letters, 2017, vol. 58, # 38, p. 3743 - 3746]
[3]Wu, Yunxiang; Zhou, Bing [Organic Letters, 2017, vol. 19, # 13, p. 3532 - 3535]
[4]Yan, Yuepeng; Feng, Peng; Zheng, Qing-Zhong; Liang, Yu-Feng; Lu, Jing-Fen; Cui, Yuxin; Jiao, Ning [Angewandte Chemie - International Edition, 2013, vol. 52, # 22, p. 5827 - 5831][Angew. Chem., 2013, vol. 125, # 22, p. 5939 - 5943,5]
[5]Yamaguchi, Tomoaki; Yamaguchi, Eiji; Tada, Norihiro; Itoh, Akichika [Advanced Synthesis and Catalysis, 2015, vol. 357, # 9, p. 2017 - 2021]
[6]Thongpaen, Jompol; Schmid, Thibault E.; Toupet, Loic; Dorcet, Vincent; Mauduit, Marc; Baslé, Olivier [Chemical Communications, 2018, vol. 54, # 59, p. 8202 - 8205]
[7]Araujo Dias, Antônio Junio; Nagashima, Yuki; Tanaka, Jin; Tanaka, Ken [Journal of the American Chemical Society, 2021, vol. 143, # 30, p. 11325 - 11331]

27
[ 78-67-1 ]
[ 203065-88-7 ]
[ 1401251-46-4 ]

Yield	Reaction Conditions	Operation in experiment
53%	With oxygen; copper diacetate In acetonitrile at 135℃; for 48h; Schlenk technique; Sealed tube;

Reference： [1]Xu, Hao; Liu, Peng-Tang; Li, Yun-Hui; Han, Fu-She [Organic Letters, 2013, vol. 15, # 13, p. 3354 - 3357]

28
[ 617-86-7 ]
[ 203065-88-7 ]
[ 1450751-45-7 ]

Yield	Reaction Conditions	Operation in experiment
68%	Stage #1: 2-(4-trifluoromethylphenyl)pyridine With C₃₀H₃₄ClIrN₂ In o-xylene at 100℃; for 6h; Stage #2: triethylsilane With tert-butylethylene for 18h;
59%	Stage #1: 2-(4-trifluoromethylphenyl)pyridine With norborn-2-ene; C₃₀H₃₃IrN₂O₂ In toluene at 115℃; for 3h; Inert atmosphere; Stage #2: triethylsilane In toluene at 115℃; for 24h; Inert atmosphere;
52%	With (carbonyl)(chloro)(hydrido)tris(triphenylphosphine)ruthenium(II); norbornene; potassium acetate In toluene at 120℃; for 20h; Inert atmosphere;

52%

With norborn-2-ene; (carbonyl)(chloro)(hydrido)tris(triphenylphosphine)ruthenium(II); potassium acetate In toluene at 120℃; for 16h; Schlenk technique; Inert atmosphere;

8 Embodiment 8 of the present invention is a method for synthesizing 2-(2-(triethyl)-4-(trifluoromethyl)phenyl)pyridine, and the reaction equation is as shown in the following formula (5): In a 20 mL Shrek tube, 2-(4-trifluoromethylphenyl)pyridine (112 mg, 0.5 mmo1), triethyl group was added in sequence.Silane (232mg, 2.0mmo1), potassium acetate (15mg, 0.15mmo1), norbornene (200μL, 2.0mmo1), tris(triphenyl)Phosphonium carbonyl ruthenium hydrochloride (23.8 mg, 0.025 mmol) in toluene (1 mL) under nitrogen at a reaction temperature of 120 ° CThe reaction was carried out under electromagnetic stirring (rotation number 500-800 rpm/min), and the reaction time was 16 hours. After the reaction is completed, the solvent is steamed by rotation.The hair is removed and the mixture is separated by column chromatography.The eluent was ethyl acetate and petroleum ether. After separation, a pale yellow liquid was obtained (88 mg).52%).

Reference： [1]Chen, Qi-Long; Dai, Kun-Long; Lu, Ka; Peng, Meng; Tu, Yong-Qiang; Yan, Zhi-Bo; Zhang, Fu-Min; Zhang, Xiao-Ming [Chemical Science, 2021, vol. 12, # 28, p. 9748 - 9753]
[2]Choi, Gyeongshin; Tsurugi, Hayato; Mashima, Kazushi [Journal of the American Chemical Society, 2013, vol. 135, # 35, p. 13149 - 13161]
[3]Liu, Shun; Lin, Qiao; Liao, Chunshu; Chen, Jing; Zhang, Kun; Liu, Qiang; Li, Bin [Organic and Biomolecular Chemistry, 2019, vol. 17, # 16, p. 4115 - 4120]
[4]Current Patent Assignee: WUYI UNIVERSITY - CN109651421, 2019, A Location in patent: Paragraph 0065-0073

29
[ 22664-13-7 ]
[ 203065-88-7 ]
2-{4-trifluoromethyl-2-[(cis-2-phenylcyclopropyl)methyl]phenyl}pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89%	With [Ru(O₂CMes)₂(p-cymene)]; potassium 2,4,6-trimethylbenzoate In 1,4-dioxane at 120℃; for 48h; Inert atmosphere; chemoselective reaction;

Reference： [1]Schinkel, Marvin; Wallbaum, Jan; Kozhushkov, Sergei I.; Marek, Ilan; Ackermann, Lutz [Organic Letters, 2013, vol. 15, # 17, p. 4482 - 4484]

30
[ 54376-39-5 ]
[ 203065-88-7 ]
[ 1450758-88-9 ]
[ 1450758-89-0 ]

Yield	Reaction Conditions	Operation in experiment
1: 47% 2: 31%	With [Ru(O₂CMes)₂(p-cymene)]; potassium 2,4,6-trimethylbenzoate In toluene at 120℃; for 48h; Inert atmosphere; chemoselective reaction;

Reference： [1]Schinkel, Marvin; Wallbaum, Jan; Kozhushkov, Sergei I.; Marek, Ilan; Ackermann, Lutz [Organic Letters, 2013, vol. 15, # 17, p. 4482 - 4484]

31
[ 70-55-3 ]
[ 203065-88-7 ]
[ 1379667-23-8 ]

Yield	Reaction Conditions	Operation in experiment
90%	With silver hexafluoroantimonate; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; [bis(acetoxy)iodo]benzene In dichloromethane at 60℃; for 24h; Schlenk technique; Inert atmosphere;

Reference： [1]Zhao, Huaiqing; Shang, Yaping; Su, Weiping [Organic Letters, 2013, vol. 15, # 19, p. 5106 - 5109]

32
[ 203065-88-7 ]
[ 98-80-6 ]
4'-(trifluoromethyl)-1,1':2',1''-terphenyl [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
41%	With tert.-butylhydroperoxide; palladium diacetate; copper(II) bis(trifluoromethanesulfonate) In acetonitrile at 60℃; for 24h; Sealed tube;	General Procedure for the Arylation of indoles General procedure: A sealed tube was charged with 2-phenylpyridine (1; 68.0 mg, 0.44 mmol),phenylboronic acid (2.5 equiv), Cu(OTf)2 (0.2 equiv), TBHP (2 equiv), and Pd(OAc)2(10 mol%) in acetonitrile (15 mL) The mixture was heated to 60 °C and stirred violently at this temperature for 24 h. After being cooled to room temperature, the mixture was fitered. The filtrate was evapaored under vacuum. Subsequently, the residue was purified by chromatography (silica gel, n-hexane:EtOAc, 10:1).

Reference： [1]Feng, Jie; Lu, Guoping; Lv, Meifang; Cai, Chun [Synlett, 2013, vol. 24, # 16, p. 2153 - 2159]

33
[ 1516-60-5 ]
[ 203065-88-7 ]
C₁₈H₁₂F₃N₃O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
68%	With silver hexafluoroantimonate; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer In chlorobenzene at 120℃; Schlenk technique; regioselective reaction;

Reference： [1]Tang, Conghui; Yuan, Yizhi; Cui, Yuxin; Jiao, Ning [European Journal of Organic Chemistry, 2013, # 33, p. 7480 - 7483]

34
[ 694-59-7 ]
[ 501374-30-7 ]
[ 203065-88-7 ]

Reference： [1]Chemical Communications,2014,vol. 50,p. 4292 - 4295

35
[ 582-61-6 ]
[ 203065-88-7 ]
[ 1581756-75-3 ]

Yield	Reaction Conditions	Operation in experiment
78%	With silver hexafluoroantimonate; (p-cymene)ruthenium(II) chloride; ortho-nitrobenzoic acid In 1,2-dichloro-ethane at 50℃; for 18h; chemoselective reaction;

Reference： [1]Shin, Kwangmin; Ryu, Jaeyune; Chang, Sukbok [Organic Letters, 2014, vol. 16, # 7, p. 2022 - 2025]

36
[ 85-41-6 ]
[ 203065-88-7 ]
[ 1607824-47-4 ]

Yield	Reaction Conditions	Operation in experiment
62%	With oxygen; copper (I) acetate In 1,2-dichloro-benzene; toluene at 150℃; Schlenk technique;

Reference： [1]Xu, Hui; Qiao, Xixue; Yang, Shiping; Shen, Zengming [Journal of Organic Chemistry, 2014, vol. 79, # 10, p. 4414 - 4422]

37
[ 372-48-5 ]
[ 125102-17-2 ]
[ 203065-88-7 ]

Yield	Reaction Conditions	Operation in experiment
93%	With bis(tricyclohexylphosphine)nickel(II) dichloride In tetrahydrofuran; 1-methyl-pyrrolidin-2-one at 25 - 100℃; for 20h; Schlenk technique; Inert atmosphere;

Reference： [1]Zhu, Feng; Wang, Zhong-Xia [Journal of Organic Chemistry, 2014, vol. 79, # 10, p. 4285 - 4292]

38
[ 12354-84-6 ]
[ 16836-95-6 ]
[ 203065-88-7 ]
[ 1613027-89-6 ]

Reference： [1]Organic Letters,2014,vol. 16,p. 3328 - 3331

39
bis[dichloro(pentamethylcyclopentadienyl)iridium(III)] [ No CAS ]
[ 563-63-3 ]
[ 203065-88-7 ]
[ 1613027-90-9 ]

Yield	Reaction Conditions	Operation in experiment
72%	With sodium acetate In dichloromethane at 20℃; for 12h; Inert atmosphere;

Reference： [1]Patel, Pitambar; Chang, Sukbok [Organic Letters, 2014, vol. 16, # 12, p. 3328 - 3331]

40
[ 1613027-54-5 ]
[ 203065-88-7 ]
[ 1613027-73-8 ]

Yield	Reaction Conditions	Operation in experiment
83%	With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; silver(I) 4-methylbenzenesulfonate In 1,2-dichloro-ethane at 25℃; for 10h; Inert atmosphere;

Reference： [1]Patel, Pitambar; Chang, Sukbok [Organic Letters, 2014, vol. 16, # 12, p. 3328 - 3331]

41
[ 542-18-7 ]
[ 203065-88-7 ]
2-[2,6-dicyclohexyl-4-(trifluoromethyl)phenyl]pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
39%	With 1,3-diisopropylimidazolium tetrafluoroborate; neopentylmagnesium bromide; cobalt(II) bromide In tetrahydrofuran at 20℃; for 24h; Schlenk technique;	10dr General procedure: A 10 mL Schlenk tube was charged with CoBr2 (6.6 mg, 0.03mmol), 1,3-diisopropyl-1H-benzimidazol-3-ium bromide (L4; 8.5mg, 0.03 mmol), 4-methoxy-N-[(1E)-1-phenylethylidene]aniline(1a, 67.6 mg, 0.30 mmol), 1-chlorooctane (2a, 76.5 μL, 0.45 mmol), and THF (0.69 mL). A 1.92 M solution of t-BuCH2MgBr inTHF (0.31 mL, 0.60 mmol) was added dropwise at 0 °C, and themixture was stirred at r.t. for 6 h. The reaction was quenched by theaddition of 3 M aq HCl (1.0 mL), and the mixture was stirred at r.t.for 1 h, then extracted with EtOAc (3 × 10 mL). The organic layerswere combined, dried (MgSO4), and concentrated under reduced pressure. The crude product was purified by chromatography [silicagel, hexane-EtOAc (40:1)].

Reference： [1]Gao, Ke; Yamakawa, Takeshi; Yoshikai, Naohiko [Synthesis, 2014, vol. 46, # 15, p. 2024 - 2039]

42
[ 709-63-7 ]
[ 109-76-2 ]
[ 203065-88-7 ]

Yield	Reaction Conditions	Operation in experiment
60%	With oxygen; copper(II) bis(trifluoromethanesulfonate); toluene-4-sulfonic acid In hexan-1-ol at 110℃; for 24h; Sealed tube; Schlenk technique;
45%	With oxygen; lithium chloride In N,N-dimethyl acetamide at 160℃; for 12h; Schlenk technique; Sealed tube;
14%	With tris(2,2'-bipyridyl)ruthenium dichloride; oxygen; toluene-4-sulfonic acid In acetonitrile at 82℃; for 48h; Irradiation;

Reference： [1]Xi, Long-Yi; Zhang, Ruo-Yi; Liang, Shuai; Chen, Shan-Yong; Yu, Xiao-Qi [Organic Letters, 2014, vol. 16, # 20, p. 5269 - 5271]
[2]Wu, Kun; Huang, Zhiliang; Liu, Chao; Zhang, Heng; Lei, Aiwen [Chemical Communications, 2015, vol. 51, # 12, p. 2286 - 2289]
[3]Hu, Bei; Li, Yuyuan; Dong, Wuheng; Xie, Xiaomin; Wan, Jun; Zhang, Zhaoguo [RSC Advances, 2016, vol. 6, # 54, p. 48315 - 48318]

43
[ 26386-88-9 ]
[ 203065-88-7 ]
diphenyl (2-(pyridin-2-yl)-5-(trifluoromethyl)phenyl)phosphoramidate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; silver(I) triflimide In 1,2-dichloro-ethane at 80℃; for 24h;

Reference： [1]Kim, Hyunwoo; Park, Juhyeon; Kim, Jeung Gon; Chang, Sukbok [Organic Letters, 2014, vol. 16, # 20, p. 5466 - 5469]

44
[ 135205-66-2 ]
[ 203065-88-7 ]
[ 1401251-46-4 ]

Yield	Reaction Conditions	Operation in experiment
54%	With carbonyl(pentamethylcyclopentadienyl)cobalt diiodide; silver(I) acetate; silver(I) triflimide In 1,2-dichloro-ethane at 120℃; for 12h; Inert atmosphere;

Reference： [1]Pawar, Amit B.; Chang, Sukbok [Organic Letters, 2015, vol. 17, # 3, p. 660 - 663]

45
[ 110-86-1 ]
[ 455-24-3 ]
[ 203065-88-7 ]
[ 220000-88-4 ]
[ 426823-25-8 ]

Reference： [1]Angewandte Chemie - International Edition,2015,vol. 54,p. 2199 - 2203
Angew. Chem.,2014,vol. 54-127,p. 2227 - 2231

46
iridium(III) chloride n-hydrate [ No CAS ]
[ 203065-88-7 ]
fac-tris[2-(2-pyridinyl-N)-5-(trifluouromethyl)phenyl-C] iridium (III) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%	In water at 200℃; Inert atmosphere;	General procedure B for the synthesis of homoleptic fac- Ir(C^N)₃ complexes (3a-3f,h). General procedure: A Parr reactor (1 L model 4533, Fig. S1) was charged withiridium (III) chloride (1 equiv), ligand (12 equiv), sodium carbonate(6 equiv) and DI water (0.03 M). The reaction mixture was pressurized(30 PSI) and depressurized with Ar (3) and finally charged again with Ar before sealing. The reaction mixture was heated at 200 °C for 24-48 h. After cooling to room temperature, reaction mixture was extracted with DCM (3 20 mL). The combined organic portion was filtered through celite pad which was then concentrated to obtain crude product. The pure compound 3a-3f was obtained by performing flash chromatography. For most complexes, (3a-3d) crude samples were dry loaded on silica prior to running the column due to low solubility of the complex. After elution of the ligand with hexane/ethyl acetate the eluting solvent was switched to dichloromethane, which facilitated the elution ofthe iridium complexes (3a-3f).

Reference： [1]Singh, Anuradha; Teegardin, Kip; Kelly, Megan; Prasad, Kariate S.; Krishnan, Sadagopan; Weaver, Jimmie D. [Journal of Organometallic Chemistry, 2015, vol. 776, p. 51 - 59]

47
[ 95-16-9 ]
[ 203065-88-7 ]
2-(2-(pyridin-2-yl)-5-(trifluoromethyl)phenyl)benzothiazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%	With dirhodium tetraacetate; copper(l) iodide; copper diacetate; triphenylphosphine In N,N-dimethyl acetamide at 160℃; for 9h; Inert atmosphere;	7 4.2.7 2-(2-(Pyridin-2-yl)-5-(trifluoromethyl)phenyl)benzothiazole (3ga) General procedure: Rh(OAc)2]2 (4.4 mg, 0.01 mmol), 2-phenylpyridine 1a (31 mg, 0.2 mmol), PPh3 (10.4 mg, 0.04 mmol), CuI (38.2 mg, 0.2 mmol), Cu(OAc)2 (108.6 mg, 0.6 mmol), N,N-dimethylacetamide (2.0 mL) were placed inside a 10 mL Schlenk tube equipped with a reflux condenser. Then, the temperature was risen to 160 °C. Benzothiazole 2a (81 mg, 0.6 mmol) was separated into five portions and each portion was added within 1 h. After finishing addition, the solution was stirred under argon atmosphere at 160 °C for another 4 h. After cooling to room temperature, the reaction mixture was quenched with ethyl acetate (15 mL) and washed with water (30 mL). The aqueous phase was extracted twice with EtOAc (3*10 mL), and the combined organic layer was dried over anhydrous Na2SO4. After evaporation of the solvents in vacuo, the crude product was purified by column chromatography on silica gel (petroleum ether/EtOAc=3/1) to give desire product Yield: 76%. Yellow oil. 1H NMR (600 MHz, CDCl3) δ 8.64 (d, J=4.5 Hz, 1H), 8.27 (s, 1H), 8.01 (d, J=8.2 Hz, 1H), 7.81 (d, J=8.0 Hz, 1H), 7.79-7.73 (m, 2H), 7.60 (t, J=7.7 Hz, 1H), 7.45 (t, J=7.6 Hz, 1H), 7.37-7.25 (m, 3H); 13C NMR (150 MHz, CDCl3) δ 165.9, 157.1, 153.2, 145.0, 136.7, 136.4, 133.7, 131.4, 127.34 (q, J=148.5 Hz), 125.6, 125.2, 123.8, 123.1, 121.6; IR (KBr) ν=3061, 1587, 1522, 1492, 1457, 1404, 1331, 1260, 1211, 1129, 1085, 1037, 899, 792, 758, 728, 704 cm-1; HRMS: calcd for C19H11F3N2S: 356.0595, found: 356.0590.

Reference： [1]Liu, Hui; Xu, Huan; Yuan, Yu [Tetrahedron, 2014, vol. 70, # 37, p. 6474 - 6481]

48
[ 140-10-3 ]
[ 203065-88-7 ]
(E)-2-(2,6-distyryl-4-trifluoromethyl-phenyl)pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
93%	With bis(1,5-cyclooctadiene)rhodium(I) trifluoromethanesulfonate; 2,2-dimethylpropanoic anhydride In toluene at 140℃; for 12h; Inert atmosphere;

Reference： [1]Qiu, Ruiying; Zhang, Lingjuan; Xu, Conghui; Pan, Yixiao; Pang, Hongze; Xu, Lijin; Li, Huanrong [Advanced Synthesis and Catalysis, 2015, vol. 357, # 6, p. 1229 - 1236]

49
[ 1013-91-8 ]
[ 203065-88-7 ]
2-(2-(fluorodiphenylsilyl)-4-(trifluoromethyl)phenyl)pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%	With norborn-2-ene; iridium(I)-(1,5-cyclooctadiene)-acetylacetonate In toluene at 115℃; for 24h; Inert atmosphere; regioselective reaction;

Reference： [1]Wakaki, Takayuki; Kanai, Motomu; Kuninobu, Yoichiro [Organic Letters, 2015, vol. 17, # 7, p. 1758 - 1761]

50
[ 6773-29-1 ]
[ 203065-88-7 ]
methyl 6-oxo-9-(trifluoromethyl)-6H-pyrido[2,1-a]isoquinoline-7-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86%	With carbonyl(η-5-cyclopentadienyl)diiodocobalt(III); Ag⁽¹⁺⁾*(x)F₆Sb; potassium acetate In 2,2,2-trifluoroethanol at 120℃; for 24h; Inert atmosphere; Schlenk technique;

Reference： [1]Zhao, Dongbing; Kim, Ju Hyun; Stegemann, Linda; Strassert, Cristian A.; Glorius, Frank [Angewandte Chemie - International Edition, 2015, vol. 54, # 15, p. 4508 - 4511][Angew. Chem., 2015, vol. 127, # 15, p. 4591 - 4594,4]

51
[ 1666-13-3 ]
[ 203065-88-7 ]
2-(2,6-bis(phenylselanyl)-4-(trifluoromethyl)phenyl)pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
68%	Stage #1: 2-(4-trifluoromethylphenyl)pyridine With bis(benzonitrile)palladium(II) dichloride In dimethyl sulfoxide at 20℃; for 0.166667h; Inert atmosphere; Schlenk technique; Stage #2: diphenyl diselenide In dimethyl sulfoxide at 140℃; for 12h; Inert atmosphere; Schlenk technique;

Reference： [1]Iwasaki, Masayuki; Tsuchiya, Yuta; Nakajima, Kiyohiko; Nishihara, Yasushi [Organic Letters, 2014, vol. 16, # 18, p. 4920 - 4923]

52
[ 19226-36-9 ]
[ 203065-88-7 ]
[ 1581756-75-3 ]

Yield	Reaction Conditions	Operation in experiment
95%	With [(1,2,3,4,5-pentamethylcyclopentadienyl)*Co(CH₃CN)₃](SbF₆)₂ In 1,2-dichloro-ethane at 80℃; for 12h;
90%	With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; silver(I) triflimide In 1,2-dichloro-ethane at 40℃; for 12h; Autoclave;
72%	With bromopentacarbonylmanganese(I) at 50℃; for 4h; Ionic liquid;	4. General procedure for the Mn-Catalyzed amidations General procedure: Starting material 1 (0.2 mmol), dioxazolones 2 (0.21 mmol), MnBr(CO)5 (2.5 mol %) and [Hmim]OAc (1 mL) were added to an oven-dried 25 mL-vial equipped with a stir bar, The reaction mixture was stirred in a pre-heated oil bath at 50 oC for 4 h in an oil bath with vigorous stirring. Upon completion, the mixture was diluted with H2O. The layer was separated, and the aqueous layer was extracted with ethyl acetate (10 mL 3). The combined organic layers were dried over MgSO4. The solvents were removed under reduced pressure, and the crude reaction mixture was purified by chromatography on silica gel (n-hexanes/EtOAc) as an eluent to give the desired product 3. Reuse of MnBr(CO)5/[Hmim]OAc catalytic system. The reaction was set up the same as above. After the reaction was complete, diethyl ether (20 mL) was added to extract the product 3 from the reaction mixture, the ionic liquid containing the Mn catalyst was separated and could be used for next reaction without further treatment. After removal of excess ether solvent, the product 3 was purified by chromatography on silica gel (n-hexanes/EtOAc) as an eluent.

54%

With C₂₂H₂₈Cl₂InNRh⁽¹⁺⁾*C₃₂H₁₂BF₂₄^(1-) In toluene at 120℃; for 4h; Inert atmosphere;

Reference： [1]Liang, Yujie; Liang, Yu-Feng; Tang, Conghui; Yuan, Yizhi; Jiao, Ning [Chemistry - A European Journal, 2015, vol. 21, # 46, p. 16395 - 16399]
[2]Park, Yoonsu; Park, Kyung Tae; Kim, Jeung Gon; Chang, Sukbok [Journal of the American Chemical Society, 2015, vol. 137, # 13, p. 4534 - 4542]
[3]Kong, Xianqiang; Xu, Bo [Tetrahedron Letters, 2020, vol. 61, # 8]
[4]Yamada, Ryosuke; Iwasawa, Nobuharu; Takaya, Jun [Angewandte Chemie - International Edition, 2019, vol. 58, # 48, p. 17251 - 17254][Angew. Chem., 2019, vol. 131, # 48, p. 17411 - 17414,4]

53
[ 23847-33-8 ]
[ 203065-88-7 ]
2-(2,6-bis(phenylthio)-4-(trifluoromethyl)phenyl)pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87%	With dichloro bis(acetonitrile) palladium(II) In N,N-dimethyl-formamide at 120℃; for 24h; Inert atmosphere;	42 General procedure for the palladium-catalyzed C-H sulfenylation General procedure: Under N2 atmosphere, an oven-dried reaction vessel was charged with 2-arylpyridine 1 (0.3mmol), N-(arylthio)benzamide 2 (0.45mmol for monothiolation and 1.2mmol for dithiolation), Pd(MeCN)2Cl2 (0.03mmol) and dry DMF (2mL). The vessel was sealed and heated at 120°C (oil bath temperature) for 24h and then cooled to room temperature. Brine and ethyl acetate were added to the reaction mixture. The mixture was extracted with ethyl acetate three times, and the combined organic layer was dried over MgSO4. After removal of the solvent under reduced pressure, the residue was purified by silica-gel column chromatography to give the products.

Reference： [1]Zhang, Xing-Song; Li, Guoxing; Zhang, Xing-Guo; Zhang, Xiao-Hong [Tetrahedron, 2015, vol. 71, # 34, p. 5458 - 5464]

54
[ 23847-33-8 ]
[ 203065-88-7 ]
[ 1609120-82-2 ]

Yield	Reaction Conditions	Operation in experiment
62%	With dichloro bis(acetonitrile) palladium(II) In N,N-dimethyl-formamide at 120℃; for 24h; Inert atmosphere;	20 General procedure for the palladium-catalyzed C-H sulfenylation General procedure: Under N2 atmosphere, an oven-dried reaction vessel was charged with 2-arylpyridine 1 (0.3mmol), N-(arylthio)benzamide 2 (0.45mmol for monothiolation and 1.2mmol for dithiolation), Pd(MeCN)2Cl2 (0.03mmol) and dry DMF (2mL). The vessel was sealed and heated at 120°C (oil bath temperature) for 24h and then cooled to room temperature. Brine and ethyl acetate were added to the reaction mixture. The mixture was extracted with ethyl acetate three times, and the combined organic layer was dried over MgSO4. After removal of the solvent under reduced pressure, the residue was purified by silica-gel column chromatography to give the products.

Reference： [1]Zhang, Xing-Song; Li, Guoxing; Zhang, Xing-Guo; Zhang, Xiao-Hong [Tetrahedron, 2015, vol. 71, # 34, p. 5458 - 5464]

55
[ 2835-06-5 ]
[ 203065-88-7 ]
[ 1236046-63-1 ]

Yield	Reaction Conditions	Operation in experiment
78%	With dipotassium peroxodisulfate; water; copper diacetate; palladium diacetate In dimethyl sulfoxide at 120℃; for 24h; Inert atmosphere;	Synthesis of 3a-v General procedure: A mixture of 1 (0.5 mmol), 2 (0.6 mmol), DMSO (5% H2O aq, 5mL), Pd(OAc)2 (5 mol%), Cu(OAc)2 (10 mol%), and K2S2O8 (2equiv) was stirred at 120 °C under Ar atmosphere for 24 h. Thereaction mixture was washed with H2O, and the aqueous phasewas extracted with EtOAc (3×). The combined organic layer waswashed with brine, dried over Na2SO4, and evaporated underreduced pressure. The crude product was purified by silica gelcolumn chromatography to give the corresponding products(3a-d,7b 3f-k,7b 3n-s7b).

Reference： [1]Fan, Weizheng; Su, Jiapeng; Feng, Bainian [Synlett, 2015, vol. 26, # 14, p. 2033 - 2036]

56
[ 150176-08-2 ]
[ 203065-88-7 ]
7-(pyridin-2-yl)-9-(trifluoromethyl)-6H-pyrido[2,1-a]isoquinolin-6-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With [Cp*Rh(CH₃CN)₃](SbF₆)₂ In 2,2,2-trifluoroethanol at 140℃; for 24h; Inert atmosphere; Schlenk technique; Sealed tube;

Reference： [1]Kim, Ju Hyun; Gensch, Tobias; Zhao, Dongbing; Stegemann, Linda; Strassert, Cristian A.; Glorius, Frank [Angewandte Chemie - International Edition, 2015, vol. 54, # 37, p. 10975 - 10979][Angew. Chem., 2015, vol. 127, # 37, p. 11126 - 11130,5]

57
[ 1282034-09-6 ]
[ 125102-17-2 ]
[ 203065-88-7 ]

Yield	Reaction Conditions	Operation in experiment
82%	With 1-Methylpyrrolidine; C₂₀H₂₀ClN₃Ni In tetrahydrofuran at 50℃; for 12h; Schlenk technique; Inert atmosphere;

Reference： [1]Tao, Jian-Long; Wang, Zhong-Xia [European Journal of Organic Chemistry, 2015, vol. 2015, # 29, p. 6534 - 6540]

58
1-(benzoyl)piperidine-2,6-dione [ No CAS ]
[ 203065-88-7 ]
[ 1048643-97-5 ]

Yield	Reaction Conditions	Operation in experiment
74%	With chloro(1,5-cyclooctadiene)rhodium(I) dimer In toluene at 150℃; for 15h; Schlenk technique; Inert atmosphere; regioselective reaction;

Reference： [1]Meng, Guangrong; Szostak, Michal [Organic Letters, 2016, vol. 18, # 4, p. 796 - 799]

59
[ 127827-58-1 ]
[ 128796-39-4 ]
[ 203065-88-7 ]

Yield	Reaction Conditions	Operation in experiment
97%	With [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene](3-chloropyridyl)palladium(ll) dichloride; potassium carbonate In ethanol; water at 35℃; for 4h; chemoselective reaction;

Reference： [1]Zhang, Enxuan; Tang, Jiaze; Li, Suhua; Wu, Peng; Moses, John E.; Sharpless, K. Barry [Chemistry - A European Journal, 2016, vol. 22, # 16, p. 5692 - 5697]

60
[ 71098-88-9 ]
[ 203065-88-7 ]
2-(2-(phenylselanyl)-4-(trifluoromethyl)phenyl)pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
84%	With dichloro bis(acetonitrile) palladium(II) In water; dimethyl sulfoxide at 100℃; for 24h; Sealed tube; regioselective reaction;	4.3General procedure for the diselenylation: synthesis of compound 3 General procedure: A mixture of arenes 1 (0.10mmol), N-PSP 2a (71mg, 0.20mmol), PdCl2(CH3CN)2 (3mg, 0.01mmol) and DMSO/H2O mixed solvents (v/v=1:1, 1.0mL) was added to a 25mL sealed tube under air atmosphere, then stirred at 100°C for 24h. After cooling to ambient temperature, the resulting mixture was extracted with EtOAc (3×10mL). The combined organic phase was dried over anhydrous MgSO4, filtered, and all the volatiles were evaporated under reduced pressure. The resultant residue was purified by silica gel column chromatography (eluent: petroleum ether (35-60°C)/Et2O=30:1, v/v) to afford the desired products 3 as a white solid.

Reference： [1]Jin, Weiwei; Zheng, Poonnapa; Law, Ga-Lai; Wong, Wing-Tak [Journal of Organometallic Chemistry, 2016, vol. 812, p. 66 - 73]

61
[ 71098-88-9 ]
[ 203065-88-7 ]
2-(2,6-bis(phenylselanyl)-4-(trifluoromethyl)phenyl)pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
91%	With dichloro bis(acetonitrile) palladium(II) In water; dimethyl sulfoxide at 100℃; for 24h; Sealed tube; regioselective reaction;	4.3General procedure for the diselenylation: synthesis of compound 4 General procedure: A mixture of arenes 1 (0.10mmol), N-PSP 2a (71mg, 0.20mmol), PdCl2(CH3CN)2 (3mg, 0.01mmol) and DMSO/H2O mixed solvents (v/v=4:1, 1.0mL) was added to a 25mL sealed tube under air atmosphere, then stirred at 100°C for 24h. After cooling to ambient temperature, the resulting mixture was extracted with EtOAc (3×10mL). The combined organic phase was dried over anhydrous MgSO4, filtered, and all the volatiles were evaporated under reduced pressure. The resultant residue was purified by silica gel column chromatography (eluent: petroleum ether (35-60°C)/Et2O=30:1, v/v) to afford the desired products 4 as a white solid.

Reference： [1]Jin, Weiwei; Zheng, Poonnapa; Law, Ga-Lai; Wong, Wing-Tak [Journal of Organometallic Chemistry, 2016, vol. 812, p. 66 - 73]

62
[ 271-58-9 ]
[ 203065-88-7 ]
2-((2-(pyridin-2-yl)-5-(trifluoromethyl)phenyl)amino)benzaldehyde [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
50%	With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; silver(I) triflimide; Trimethylacetic acid In 1,2-dichloro-ethane at 100℃; for 24h; Schlenk technique;

Reference： [1]Zou, Miancheng; Liu, Jianzhong; Tang, Conghui; Jiao, Ning [Organic Letters, 2016, vol. 18, # 12, p. 3030 - 3033]

63
[ 924-44-7 ]
[ 203065-88-7 ]
ethyl 8-(trifluoromethyl)pyrido[2,1-α]isoindole-6-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	With silver hexafluoroantimonate; carbonyl(pentamethylcyclopentadienyl)cobalt diiodide; copper diacetate In 1,2-dichloro-ethane at 110℃; for 24h; Inert atmosphere; Sealed tube;

Reference： [1]Chen, Xun; Hu, Xinwei; Deng, Yuanfu; Jiang, Huanfeng; Zeng, Wei [Organic Letters, 2016, vol. 18, # 18, p. 4742 - 4745]

64
[ 10025-99-7 ]
[ 123-54-6 ]
[ 203065-88-7 ]
C₁₇H₁₄F₃NO₂Pt [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70.4%	Stage #1: potassium tetrachloroplatinate(II); 2-(4-trifluoromethylphenyl)pyridine In water at 100℃; for 12h; Inert atmosphere; Stage #2: acetylacetone With sodium carbonate In water at 100℃; for 13h; Inert atmosphere;	12.2 Synthesis of Compound 12 Synthesis of the complex:To a round bottom two-necked flask was added potassium tetrachloroplatinate (0.2 mmo 1)A mixed solution of 2- (4-trifluoromethylphenyl) pyridine (0.24 mmol) and 6 mL / 2 mL of ethylene glycol monoethyl ether / water,Nitrogen under the protection of magnetic stirring 100 ° C 12h,After the reaction,Respectively, with hexane,Ethanol washing filter cake,To give the dichloro-bridge intermediate.The resulting dichloro-bridge intermediate was added to a single-necked round bottom flask,Sodium carbonate (1.0 mmol),Acetyl acetone (2. Ommo 1) and 6 mL of ethylene glycol monoethyl ether,Nitrogen under the protection of magnetic stirring at 100 ° C for 13h,After completion of the reaction, the reaction mixture was evaporated in vacuo and separated by column chromatography to obtain analytically pure compounds12. The structure of the product was identified by mass spectrometry, and the isolation yield was 70.4%.

Reference： [1]Current Patent Assignee: DALIAN UNIVERSITY OF TECHNOLOGY - CN103145763, 2016, B Location in patent: Paragraph 0077; 0079

65
[ 26838-86-8 ]
[ 128796-39-4 ]
[ 203065-88-7 ]

Yield	Reaction Conditions	Operation in experiment
87%	With palladium diacetate; sodium carbonate; 1,2-bis-(dicyclohexylphosphino)ethane In toluene at 130℃; Inert atmosphere; Schlenk technique;

Reference： [1]Muto, Kei; Hatakeyama, Taito; Itami, Kenichiro; Yamaguchi, Junichiro [Organic Letters, 2016, vol. 18, # 19, p. 5106 - 5109]

66
[ 10025-99-7 ]
[ 203065-88-7 ]
C₂₄H₁₄Cl₂F₆N₂Pt₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In 2-ethoxy-ethanol; water at 80℃; for 16h;
	In 2-ethoxy-ethanol; water at 80℃; for 16h;	1 A mixture of platinum salt K2PtCl4 (0.415 g, 1 mmol) and 2-(4-trifluoromethyl)phenylpyridine (2.5 mmol, 0.475 g) was added to a mixed solvent of 2-ethoxyethanol and water (3: 1, v / v). The reaction was stirred at 80 °C for 16 hours, precipitate platinum is the bridged dimeric complexes.
	In 2-ethoxy-ethanol

Reference： [1]Lu, Guang-Zhao; Li, Yan; Jing, Yi-Ming; Zheng, You-Xuan [Dalton Transactions, 2017, vol. 46, # 1, p. 150 - 157]
[2]Current Patent Assignee: NANJING UNIVERSITY; AAC ACOUSTIC TECHNOLOGIES HOLDINGS INC. - CN106632492, 2017, A Location in patent: Paragraph 0054-0056
[3]Li, Jiangang; Chen, Kexin; Wei, Juan; Ma, Yun; Zhou, Ruyi; Liu, Shujuan; Zhao, Qiang; Wong, Wai-Yeung [Journal of the American Chemical Society, 2021, vol. 143, # 43, p. 18317 - 18324]

67
[ 50-00-0 ]
[ 203065-88-7 ]
(2-(pyridin-2-yl)-5-(trifluoromethyl)phenyl)methanol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂; sodium acetate; zinc dibromide In 1,2-dichloro-ethane at 60℃; for 24h; Sealed tube; Inert atmosphere;

Reference： [1]Zhang, Guo-Fu; Li, Yue; Xie, Xiao-Qiang; Ding, Cheng-Rong [Organic Letters, 2017, vol. 19, # 5, p. 1216 - 1219]

68
[ 10025-99-7 ]
[ 203065-88-7 ]
C₂₄H₁₄Cl₂F₆N₂Pt₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In 2-ethoxy-ethanol; water at 80℃; for 16h;	2.3.5. General synthesis of Pt1-Pt4 General procedure: The K2PtCl4 (0.415 g, 1 mmol) and 1.5 equivalent of C^N ligand(1.5 mmol) were mixed in a 3:1 mixture of 2-ethoxyethanol andwater. The mixture was heated at 80 °C for 16 h. The Pt-dimer wasprecipitated in water. The resulting yellow-greenish powder wasfiltered and was subsequently reacted with Ktpip without furtherpurification. A stirred mixture of Pt-dimer (0.30 g, 0.33 mmol) andKtpip (0.99 mmol, 0.45 g) in 2-ethoxyethanol (25 mL)was heated at80 °C for 16 h. After cooling the mixture to room temperature, thesolution was concentrated under reduced pressure. The resultingresiduewas subjected to column chromatography (silica gel, CH2Cl2/petroleum ether 1:2 (v/v)) to give product as a yellow solid, whichwas further purified by sublimation in vacuum.

Reference： [1]Lu, Guang-Zhao; Han, Hua-Bo; Li, Yan; Zheng, You-Xuan [Dyes and Pigments, 2017, vol. 143, p. 33 - 41]

69
[ 203065-88-7 ]
[ 94-05-3 ]
[ 1401251-46-4 ]

Yield	Reaction Conditions	Operation in experiment
81%	With oxygen; copper diacetate In N,N-dimethyl-formamide at 130℃; for 12h;

Reference： [1]Qi, Chaorong; Hu, Xiaohan; Jiang, Huanfeng [Chemical Communications, 2017, vol. 53, # 57, p. 7994 - 7997]

70
9-borabicyclo-[3.3.1]nonane dimer [ No CAS ]
[ 203065-88-7 ]
2-[2-(9-borabicyclo[3.3.1]-9-nonyl)-4-trifluoromethylphenyl]pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
56%	With ferric(III) bromide In 1,2-dichloro-ethane at 90℃; for 24h; Inert atmosphere; regioselective reaction;

Reference： [1]Yoshigoe, Yusuke; Kuninobu, Yoichiro [Organic Letters, 2017, vol. 19, # 13, p. 3450 - 3453]

71
[ 1215074-30-8 ]
[ 203065-88-7 ]

Yield	Reaction Conditions	Operation in experiment
88%	With hydrogen; triethylamine In methanol; water at 120℃; for 72h; Autoclave;

Reference： [1]Sahoo, Basudev; Surkus, Annette-Enrica; Pohl, Marga-Martina; Radnik, Jörg; Schneider, Matthias; Bachmann, Stephan; Scalone, Michelangelo; Junge, Kathrin; Beller, Matthias [Angewandte Chemie - International Edition, 2017, vol. 56, # 37, p. 11242 - 11247][Angew. Chem., 2017, vol. 129, # 37, p. 11394 - 11399]

72
[ 135364-97-5 ]
[ 203065-88-7 ]
[ 1048643-97-5 ]

Yield	Reaction Conditions	Operation in experiment
61%	With chloro(1,5-cyclooctadiene)rhodium(I) dimer; tributyl-amine; water In toluene at 150℃; for 15h; chemoselective reaction;

Reference： [1]Meng, Guangrong; Szostak, Michal [ACS Catalysis, 2017, vol. 7, # 10, p. 7251 - 7256]

73
[ 402-43-7 ]
[ 24367-66-6 ]
[ 203065-88-7 ]

Yield	Reaction Conditions	Operation in experiment
83%	With palladium diacetate; potassium carbonate; tricyclohexylphosphine In 1,4-dioxane at 150℃;

Reference： [1]Markovic, Tim; Rocke, Benjamin N.; Blakemore, David C.; Mascitti, Vincent; Willis, Michael C. [Chemical Science, 2017, vol. 8, # 6, p. 4437 - 4442]

74
[ 109-09-1 ]
[ 501374-30-7 ]
[ 203065-88-7 ]

Reference： [1]Organometallics,2017,vol. 36,p. 4363 - 4366

75
[ 131-62-4 ]
[ 203065-88-7 ]
C₂₆H₁₄F₃I₂NO₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
67%	With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; copper(II) bis(trifluoromethanesulfonate) In 1,2-dichloro-ethane at 90℃; for 12h;	General procedure: [Cp*RhCl2]2 (2.5 mol %), Cu(OTf)2 (5 mol %), 1a (0.2 mmol), 2a (0.6 mmol, 3 equiv) and DCE (2 mL) were added to a test tube. The reaction mixture was stirred at 90 oC for 12 h. After that, the solvent was removed under reduced pressure and the residue was purified by silica gel chromatography using PE/EA (5:1) to afford the title compound 4a.

Reference： [1]Jin, Chen; Wang, Guimin; Yang, Xueyan; Zhu, Weiliang; Yang, Yaxi [Tetrahedron Letters, 2018, vol. 59, # 21, p. 2042 - 2045]

76
[ 6628-07-5 ]
[ 203065-88-7 ]
2-(2,6-diallyl-4-(trifluoromethyl)phenyl)pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
69%	With [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂; silver(I) acetate In 2,2,2-trifluoroethanol at 75℃; for 12h; Inert atmosphere; Schlenk technique;

Reference： [1]Yan, Rui; Wang, Zhong-Xia [Organic and Biomolecular Chemistry, 2018, vol. 16, # 21, p. 3961 - 3969]

77
[ 100-52-7 ]
[ 203065-88-7 ]
[ 1236046-63-1 ]

Yield	Reaction Conditions	Operation in experiment
72%	With tert.-butylhydroperoxide In toluene at 110℃; for 18h; Inert atmosphere;
71%	With tert.-butylhydroperoxide; palladium diacetate In decane at 120℃; for 22.5h;	Method A: Synthesis of Pyridyl Ketones General procedure: will be illustrated with a specific example. An oven-dried 35 mL pressure tube was charged with palladium (II) acetate (0.124 g, 0.54 mmol). 2-phenylpyridine (1.87 g, 12.0 mmol) and 4-(methylthio)benzaldehyde (1.64g, 10.8 mmol) were added via syringe. The reaction was immersed in a 120 °C oil bath. Tert-butyl hydroperoxide (5-6M in decane, 3.3mL, 18.2 mmol) was added dropwise via syringe in 3 portions over 30 minutes. The reaction was kept at 120 °C and stirred for 22 hours. The reaction mixture was diluted with ethyl acetate (75 mL) and vacuum filtered through a silica gel plug. The mixture was washed with sat. NaHCO3 (50 mL) and sat. NaCl (50 mL), dried over Na2SO4, and concentrated under reduced pressure. The crude product was purified by column chromatography (hexane:EtOAc gradient) to provide the desired product 1d as an orange solid in 61 % yield.

Reference： [1]Hu, Qiyan; Liu, Xiaowang; Huang, Fei; Wang, Feifan; Li, Qian; Zhang, Wu [Catalysis Communications, 2018, vol. 113, p. 27 - 31]
[2]Johnson, Jeffrey B.; Salisbury, Eric A.; Schoonover, Erik J.; VanderRoest, Jacob P.; Wagner, Cole J. [Tetrahedron Letters, 2021, vol. 73]

78
[ 123-11-5 ]
[ 203065-88-7 ]
C₂₀H₁₄F₃NO₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
68%	With tert.-butylhydroperoxide In toluene at 110℃; for 18h; Inert atmosphere;

Reference： [1]Hu, Qiyan; Liu, Xiaowang; Huang, Fei; Wang, Feifan; Li, Qian; Zhang, Wu [Catalysis Communications, 2018, vol. 113, p. 27 - 31]

79
[ 73183-34-3 ]
[ 203065-88-7 ]
2-[2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-4-(trifluoromethyl)phenyl]pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88%	With chloro(1,5-cyclooctadiene)rhodium(I) dimer; C₂₆H₃₆N₃⁽¹⁺⁾*BF₄^(1-); potassium <i>tert</i>-butylate In hexane at 25℃; for 24h; Inert atmosphere; Glovebox;	4.2 Synthesis of products General procedure: In a nitrogen-filled glovebox, to an oven-dried 25-mL Schlenk tube was charged with [Rh(COD)Cl]2 (2.5mg, 2.5mol%), L6 (4.8mg, 5.0mol%) and KOtBu (1.1mg, 5.0mol%) and n-hexane (1.0mL). The reaction mixture was allowed to stir for 2h at room temperature, followed by adding 1a (0.2mmol) and B2pin2 (50.8mg, 0.2mmol, 1.0 equiv). The reaction was then stirred for the determined time at 25°C. The solvent was concentrated under vacuum, and the product was isolated by short-column chromatography (petroleum ether/ethyl acetate/triethylamine 4:1:1% to ethyl acetate/triethylamine 1:1%) on neutral Al2O3 (300-400 mesh). The reactions were repeated two runs.
	Stage #1: bis(pinacol)diborane With C₂₈H₃₈ClN₂O₂Rh; sodium methylate In benzene for 0.166667h; Glovebox; Schlenk technique; Inert atmosphere; Stage #2: 2-(4-trifluoromethylphenyl)pyridine at 80℃; for 16h; Schlenk technique; Sealed tube; Inert atmosphere;
62 %Spectr.	With [RhCl₂(p-cymene)]2; C₃₃H₁₈F₆IrN₃⁽³⁺⁾; sodium t-butanolate In tetrahydrofuran at 20℃; for 48h; Sealed tube; Inert atmosphere; Irradiation;

Reference： [1]Zhong, Lei; Zong, Zhi-Hong; Wang, Xi-Cun [Tetrahedron, 2019, vol. 75, # 17, p. 2547 - 2552]
[2]Thongpaen, Jompol; Schmid, Thibault E.; Toupet, Loic; Dorcet, Vincent; Mauduit, Marc; Baslé, Olivier [Chemical Communications, 2018, vol. 54, # 59, p. 8202 - 8205]
[3]Araujo Dias, Antônio Junio; Nagashima, Yuki; Tanaka, Jin; Tanaka, Ken [Journal of the American Chemical Society, 2021, vol. 143, # 30, p. 11325 - 11331]

80
iridium(III) chloride [ No CAS ]
[ 203065-88-7 ]
fac-tris[2-(2-pyridinyl-N)-5-(trifluouromethyl)phenyl-C] iridium (III) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
67.58%	In water at 205℃; for 48h; Inert atmosphere;	7 Example 7 - Synthesis of (0174) fac-Tris[2-(2-pyridinyl-N)-5-(trifluoromethyl)phenyl-Cliridium(lll) Photocatalyst (FIG.24) [0161] Iridium (III) chloride anhydrous (1.16 g, 3.89 mmol, 1 equiv), 2-(4- trifluoromethyl phenyl)-pyridine (10.4 g, 46.6 mmol, 12.0 equiv), and 1.16 L of Dl water (0.003 M with respect to IrCU) were added to a 1 L Parr reactor. The reaction mixture was pressurized with argon (10.0 psi), stirred, and then depressurized three times, and finally charged again with argon before sealing. The reaction mixture was heated to 205°C for 48 h. Then the reactor was cooled, and the reactor was opened after cooling, revealing an insoluble yellow solid on the surfaces and dispersed in the aqueous phase. All contents were transferred slowly to a 4 L separatory funnel aided by a large 5 cm glass funnel. Then the interior of the reactor was mechanically scraped (to extract the yellow material) with metal tongs, cotton balls, and acetone (100 mL) was used to remove residual compound(s) from the Parr reactor and transferred to a different 250 mL round bottom flask and concentrated down. (0176) [0162] The solid was placed on a filter frit and washed with 1 M HCI to wash away ligand. Yellow solid from the frit was taken into 200 mL of acetone and dry loaded with 40 g of silica and column ran with 5-6 column volumes to separate remaining ligand. The column was then run with 60:40 Hexanes:EtOAc to pull of dimer, and then the solvent system was switched to 100% DCM to recover the catalyst as a yellow solid in 67.58 % yield, 2.26 g. (0177) [0163] FIG.25 -- *H NMR(Chloroform-d, 400 MHz): δ = 7.99 (d, 3H, J = 8.3 Hz), 7.77-7.69 (m, 6H), 7.55 (dd, 6H, J = 6.0, 1.3 Hz), 7.20-7.15 (m, 3H), 7.02 (ddd, 3H, J = 7.1, 5.2, 1.1 Hz), 6.96 (b, 3H) ppm.13C NMR (Methylene Chloride-d2, 101 MHz): δ = 165.0, 159.2, 147.5-147.4 (m), 147.3, 137.0.132.4 (m), 130.6, 123.9, 123.4, 120.0, 117.3-117.2 (m), 100.0. (0178) [0164] FIG.26 - 19F NMR (376 MHz, Chloroform-d) δ -62.76 (s). LC/MS (m/z) calculated for C3sH2iF9lrN3859.12 found M, 858.70.

Reference： [1]Current Patent Assignee: OKLAHOMA STATE UNIVERSITY SYSTEM - WO2018/165134, 2018, A1 Location in patent: Paragraph 0161-0164; 0165

81
[ 20718-17-6 ]
[ 203065-88-7 ]
1-phenyl-2-(2-(pyridin-2-yl)-5-(trifluoromethyl)phenyl)ethan-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
52%	With [(1,2,3,4,5-pentamethylcyclopentadienyl)*Co(CH₃CN)₃](SbF₆)₂ In 1,2-dichloro-ethane at 120℃; for 12h; Inert atmosphere; Schlenk technique;
52%	With [Cp*Co(MeCN)₃](SbF₆)₂ In 1,2-dichloro-ethane at 120℃; for 12h; Inert atmosphere; Schlenk technique;
46%	With silver hexafluoroantimonate; [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂ at 90℃; for 8h; Schlenk technique; Inert atmosphere;

Reference： [1]Ji, Shuying; Yan, Kelu; Li, Bin; Wang, Baiquan [Organic Letters, 2018]
[2]Ji, Shuying; Li, Bin; Wang, Baiquan; Yan, Kelu [Organic Letters, 2018, vol. 20, # 18, p. 5981 - 5984]
[3]Li, Huihui; Wu, Chenglin; Liu, Hong; Wang, Jiang [Journal of Organic Chemistry, 2019, vol. 84, # 21, p. 13262 - 13275]

82
[ 98-58-8 ]
[ 203065-88-7 ]
2-{2-[(4-bromophenyl)sulfonyl]-4-(trifluoromethyl)phenyl}-pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	With copper(II) acetate hydrate; palladium diacetate; silver carbonate In 1,4-dioxane at 140℃; for 16h; Schlenk technique; Inert atmosphere; chemoselective reaction;

Reference： [1]Sasmal, Arpan; Bera, Jitendra K.; Doucet, Henri; Soulé, Jean-François [European Journal of Organic Chemistry, 2018, vol. 2018, # 44, p. 6114 - 6120]

83
[ 203065-88-7 ]
2-(2-chloro-4-(trifluoromethyll)phenyl)pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65%	With tert.-butylhydroperoxide; copper(l) iodide; 1,2-dichloro-ethane at 90℃; for 24h; Sealed tube; regioselective reaction;	2. General procedure for the ortho-Chlorination General procedure: A sealed tube, equipped with a stir bar was charged with 2-phenylpyridine (1.0 equiv), TBHP (5.0 equiv), CuI (20 mol %) and 1,2-Dichloroethane (2.0 mL) was added, and the vial was closed with a screw tightly. The resulting mixture was heated in an oil bath at 90 °C for 24 h, cooled, and the mixture was extracted with EtOAc. The extract was washed with brine (2 x 15mL) and dried over Na2SO4. After evaporation, the residue was purified via column chromatography (hexanes-EtOAc) to give the corresponding product
	With N-chloro-succinimide In acetonitrile at 95℃; for 24h; Sealed tube;
40 %Chromat.	With N-chloro-succinimide In 1,2-dichloro-ethane at 95℃; for 24h; Sealed tube;

Reference： [1]Botla, Vinayak; Akudari, Ashok; Malapaka, Chandrasekharam [Tetrahedron Letters, 2019, vol. 60, # 2, p. 115 - 119]
[2]Mandal, Tanmoy; Mondal, Moumita; Choudhury, Joyanta [Organometallics, 2021, vol. 40, # 15, p. 2443 - 2449]
[3]Choudhury, Joyanta; Dutta, Tapas Kumar; Mandal, Tanmoy; Mohanty, Sunit [Chemical Communications, 2021, vol. 57, # 79, p. 10182 - 10185]

84
[ 611-73-4 ]
[ 203065-88-7 ]
C₁₉H₁₂F₃NO [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
51%	With silver (II) carbonate; sodium persulfate; dodecacarbonyl-triangulo-triruthenium; (1S)-10-camphorsulfonic acid In dichloromethane; tert-butyl methyl ether at 100℃; for 48h; Sealed tube; regioselective reaction;

Reference： [1]Jing, Kun; Li, Zhong-Yuan; Wang, Guan-Wu [ACS Catalysis, 2018, vol. 8, # 12, p. 11875 - 11881]

85
[ 50-00-0 ]
[ 203065-88-7 ]
1-(2-(pyridin-2-yl)-5-(trifluoromethyl)phenyl)ethan-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88%	With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; acetic acid; silver(I) triflimide In 2,2,2-trifluoroethanol at 120℃; for 24h; Sealed tube; Green chemistry; regioselective reaction;

Reference： [1]Wan, Ting; Du, Sidong; Pi, Chao; Wang, Yong; Li, Rongbin; Wu, Yangjie; Cui, Xiuling [ChemCatChem, 2019, vol. 11, # 16, p. 3791 - 3796]

86
2-methyl-non-2-en-4-yne [ No CAS ]
[ 203065-88-7 ]
C₂₂H₂₃F₃N⁽¹⁺⁾*F₆P^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86%	With potassium hexafluorophosphate; [Cp*Rh(OAc)₂]; copper diacetate In 2,2,2-trifluoroethanol at 50℃; regioselective reaction;
86%	With potassium hexafluorophosphate; [Cp*Rh(OAc)₂]; copper diacetate In 2,2,2-trifluoroethanol at 50℃; for 12h; Sealed tube;	13 Under air conditions, [Cp*Rh(OAc)2] (6.0 mg, 8 mol%), KPF6 (92 mg, 0.5 mmol, 2.5 eq) was added to the sealed tube.Cu(OAc)2 (20 mg, 0.1 mmol, 0.50 eq) and CF3CH2OH (2·OmL) were shaken in the dark for ten minutes, then compound 1f (0.2 mmol) and 2a compound (0.22 mmol) were added and placed in 50 °C The reaction was carried out in an oil bath. After completion of the reaction (12 hours), the sealed tube was taken out from the oil bath and cooled to ambient temperature.The reaction solution was filtered through celite.Elute with DCM:MeOH = 10:1 and concentrate.Purification by silica gel chromatography (DCM:MeOH = 20:1) 3fa, 86.0mg, 86%.

Reference： [1]Bai, Dachang; Xia, Jintao; Song, Fangfang; Li, Xueyan; Liu, Bingxian; Liu, Lihong; Zheng, Guangfan; Yang, Xifa; Sun, Jiaqiong; Li, Xingwei [Chemical Science, 2019, vol. 10, # 14, p. 3987 - 3993]
[2]Current Patent Assignee: HENAN NORMAL UNIVERSITY - CN109651366, 2019, A Location in patent: Paragraph 0084; 0085; 0086; 0087

87
[ 2446-51-7 ]
[ 203065-88-7 ]
[ 1581756-75-3 ]

Yield	Reaction Conditions	Operation in experiment
57%	With silver hexafluoroantimonate; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer In 1,2-dichloro-ethane at 140℃; for 18h; Inert atmosphere; Sealed tube;

Reference： [1]Ju, Guodong; Li, Guobao; Qian, Guanwen; Zhang, Jingyu; Zhao, Yingsheng [Organic Letters, 2019, vol. 21, # 18, p. 7333 - 7336]

88
[ 402-43-7 ]
2-(pyridin-2-yl)-2,3-dihydro-1H-naphtho[1,8-de][1,3,2]diazaborinine [ No CAS ]
[ 203065-88-7 ]

Yield	Reaction Conditions	Operation in experiment
47%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium <i>tert</i>-butylate In 1,4-dioxane at 80℃; for 21h;

Reference： [1]Yoshida, Hiroto; Seki, Michinari; Kamio, Shintaro; Tanaka, Hideya; Izumi, Yuki; Li, Jialun; Osaka, Itaru; Abe, Manabu; Andoh, Hiroki; Yajima, Tomoki; Tani, Tomohiro; Tsuchimoto, Teruhisa [ACS Catalysis, 2020, vol. 10, # 1, p. 346 - 351]

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
{[ item.p_purity ]}	{[ item.pr_size ]}	{[ getRatePrice(item.pr_usd, 1,1) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]}	{[ getRatePrice(item.pr_usd, 1,1) ]}	Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} {[ getRatePrice(item.pr_usd,1,item.mem_rate) ]}	{[ item.pr_usastock ]}	Inquiry -	{[ item.pr_chinastock ]}	Inquiry -

CAS No. :	203065-88-7	MDL No. :	MFCD08235168
Formula :	C₁₂H₈F₃N	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	KGZSSIFFYUBVOX-UHFFFAOYSA-N
M.W :	223.19	Pubchem ID :	10933075
Synonyms :

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313	UN#:	N/A
Hazard Statements:	H315-H319	Packing Group:	N/A
GHS Pictogram:

Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 203065-88-7 ] {[proInfo.proName]}

Quality Control of [ 203065-88-7 ]

Related Doc. of [ 203065-88-7 ]

Product Details of [ 203065-88-7 ]

Safety of [ 203065-88-7 ]

Application In Synthesis of [ 203065-88-7 ]

[ 203065-88-7 ] Synthesis Path-Downstream 1~88

Related Parent Nucleus of
[ 203065-88-7 ]

Pyridines

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry