[ CAS No. 113845-68-4 ]

Name: 113845-68-4|1-(4-(Trifluoromethyl)phenyl)pyrrolidine|95%
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Product Details of [ 113845-68-4 ]

CAS No. :	113845-68-4	MDL No. :	MFCD16140176
Formula :	C₁₁H₁₂F₃N	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	XAIOGMOTJLWPAJ-UHFFFAOYSA-N
M.W :	215.21	Pubchem ID :	11031229
Synonyms :

Safety of [ 113845-68-4 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P261-P301+P312-P302+P352-P304+P340-P305+P351+P338	UN#:
Hazard Statements:	H302-H315-H319-H335	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 113845-68-4 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 113845-68-4 ]

[ 113845-68-4 ] Synthesis Path-Downstream 1~29

1
[ 123-75-1 ]
[ CAS Unavailable ]
[ 113845-68-4 ]

Yield	Reaction Conditions	Operation in experiment
95%	With polymethylhydrosiloxane; sodium t-butanolate In 1,2-dimethoxyethane; toluene at 130℃; for 18h;
92%	With copper(l) iodide; C₁₄H₁₆N₂O; caesium carbonate In N,N-dimethyl-formamide at 130℃; for 24h; Inert atmosphere; Sealed tube;
91%	Stage #1: pyrrolidine; 4-chlorobenzotrifluoride With nickel(II) bromide dimethoxyethane; MTBD In N,N-dimethyl acetamide for 0.0333333h; Sonication; Stage #2: With 12,13,15,16-tetraphenyl-12,16-dihydroindeno[1,2-b]indeno[2’,1’:5,6]pyrido[3,2-g]quinoline In N,N-dimethyl acetamide at 20℃; for 36h; Irradiation;

87%	With styrene; [2,2]bipyridinyl; nickel diacetate; sodium tert-pentoxide; sodium hydride In tetrahydrofuran for 2.5h;
87%	With styrene; [2,2]bipyridinyl; sodium tert-pentoxide; sodium hydride In tetrahydrofuran for 2.5h; Heating;
87%	With carbonyl(pentamethylcyclopentadienyl)cobalt diiodide; copper diacetate In neat (no solvent) at 100℃; for 4h;
86%	With copper diacetate at 110℃; for 6h;
73%	With nickel(II) bromide dimethoxyethane; 4,4'-di-tert-butyl-2,2'-bipyridine; lithium bromide In 1,2-dimethoxyethane; N,N-dimethyl acetamide at 20℃; for 3h; Inert atmosphere; Electrochemical reaction;
71%	Stage #1: pyrrolidine With C₄₀H₅₀BrCl₂N₃Pd; potassium <i>tert</i>-butylate at 20℃; Schlenk technique; Inert atmosphere; Stage #2: 4-chlorobenzotrifluoride In toluene at 100℃; for 24h; Schlenk technique; Inert atmosphere;	16 General procedure for Pd-catalyzed amination General procedure: To a 50 mL Schlenk tube containing base (1.5 mmol) and precatalyst 4a (1 mol %, 0.0083 g) purged with N2 (three times), amine (1.2 mmol) was added via syringe, and the resulted mixture was allowed to stir at room temperature for 2-3 min. Solvent (1 mL) was then injected via syringe followed by the aryl chloride (1.0 mmol). If the aryl chloride was a solid, it was introduced into the vial prior to purging with N2. At this time, the reaction was stirred for 24 h at 100 °C. After cooling to the room temperature, the reaction mixture was concentrated in vacuo and directly purified via silica gel flash chromatography. 1-(4-(Trifluoromethyl)phenyl)pyrrolidine (14a) ;1H NMR (CDCl3, 400 MHz, 298 K): δ=7.43 (d, J=8.8 Hz, 2H), 6.54 (d, J=8.8 Hz, 2H), 3.32 (t, J=6.6 Hz, 4H), 2.03 (q, J=3.2 Hz, 4H); 13C NMR (CDCl3, 100 MHz, 298 K): δ=149.74, 126.35, 124.04, 116.68, 116.35, 110.80, 47.45, 25.39; 19F NMR (CDCl3, 400 MHz, 298 K): δ=-60.42; GC-MS: tR=16.202 min, m/z=215.1 [M]+, 214.0, 158.9, 144.9.
69%	With Ni(bpy)<SUB>3</SUB>Br<SUB>2</SUB>; tetrabutylammomium bromide; 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl acetamide at 20℃; for 4h; Electrolysis; Inert atmosphere;
66%	With Ni(COD)(DQ); sodium t-butanolate; 1,3-bis[(2,6-diisopropyl)phenyl]imidazolinium chloride at 100℃; for 24h; Sealed tube; Inert atmosphere;
71 %	With 1,4-diaza-bicyclo[2.2.2]octane; (1,2-dimethoxyethane)dichloronickel(II); 2,4,6-tris(diphenylamino)-3,5-difluorobenzonitrile In N,N-dimethyl acetamide at 20℃; Sealed tube; Inert atmosphere; Irradiation;

Reference： [1]Manolikakes, Georg; Gavryushin, Andrei; Knochel, Paul [Journal of Organic Chemistry, 2008, vol. 73, # 4, p. 1429 - 1434]
[2]Chen, Xiahong; He, Yongqiang; Liang, Yun; Liu, Wenjie; Wang, Deping; Xia, Xiaohong; Xu, Jiamin; Xu, Zhifeng; Zhang, Fuxing; Zhang, Xin [Organic Letters, 2020, vol. 22, # 19, p. 7486 - 7490]
[3]Huang, Hai; Wang, Danfeng; Zhu, Xiaolin [Chemical Communications, 2022, vol. 58, # 21, p. 3529 - 3532]
[4]Brenner, Eric; Fort, Yves [Tetrahedron Letters, 1998, vol. 39, # 30, p. 5359 - 5362]
[5]Brenner, Eric; Schneider, Raphael; Fort, Yves [Tetrahedron, 1999, vol. 55, # 44, p. 12829 - 12842]
[6]Srivastava, Avinash K.; Sharma, Charu; Joshi, Raj K. [Green Chemistry, 2020, vol. 22, # 23, p. 8248 - 8253]
[7]Joshi, Raj Kumar; Sharma, Charu; Sharma, Kamal Nayan; Srivastava, Avinash Kumar [Organic and biomolecular chemistry, 2020, vol. 18, # 18, p. 3599 - 3606]
[8]Li, Chao; Kawamata, Yu; Nakamura, Hugh; Vantourout, Julien C.; Liu, Zhiqing; Hou, Qinglong; Bao, Denghui; Starr, Jeremy T.; Chen, Jinshan; Yan, Ming; Baran, Phil S. [Angewandte Chemie - International Edition, 2017, vol. 56, # 42, p. 13088 - 13093][Angew. Chem., 2017, vol. 129, p. 13268 - 13273,6]
[9]Fang, Weiwei; Jiang, Jian; Xu, Yong; Zhou, Juefei; Tu, Tao [Tetrahedron, 2013, vol. 69, # 2, p. 673 - 679]
[10]Kawamata, Yu; Vantourout, Julien C.; Hickey, David P.; Bai, Peng; Chen, Longrui; Hou, Qinglong; Qiao, Wenhua; Barman, Koushik; Edwards, Martin A.; Garrido-Castro, Alberto F.; Degruyter, Justine N.; Nakamura, Hugh; Knouse, Kyle; Qin, Chuanguang; Clay, Khalyd J.; Bao, Denghui; Li, Chao; Starr, Jeremy T.; Garcia-Irizarry, Carmen; Sach, Neal; White, Henry S.; Neurock, Matthew; Minteer, Shelley D.; Baran, Phil S. [Journal of the American Chemical Society, 2019, vol. 141, # 15, p. 6392 - 6402]
[11]Apolinar, Omar; Derosa, Joseph; Eastgate, Martin D.; Engle, Keary M.; Joannou, Matthew V.; Li, Zi-Qi; Tran, Van T.; Wisniewski, Steven R. [Angewandte Chemie - International Edition, 2020, vol. 59, # 19, p. 7409 - 7413][Angew. Chem., 2020, vol. 132, # 19, p. 7479 - 7483,5]
[12]Gandini, Tommaso; Dolcini, Luigi; Di Leo, Lorenzo; Fornara, Matthieu; Bossi, Alberto; Penconi, Marta; Dal Corso, Alberto; Gennari, Cesare; Pignataro, Luca [ChemCatChem, 2022, vol. 14, # 23]

2
[ 123-75-1 ]
[ 25102-84-5 ]
[ 113845-68-4 ]

Yield	Reaction Conditions	Operation in experiment
92%	Stage #1: pyrrolidine; p-trifluorobenzene diazonium chloride In tetrahydrofuran; water at 0℃; for 14h; Reflux; Stage #2: With hydrogenchloride In tetrahydrofuran; diethyl ether Stage #3: With sodium hydrogencarbonate In diethyl ether; water

Reference： [1]Carpenter, Richard D.; Verkman [Organic Letters, 2010, vol. 12, # 6, p. 1160 - 1163]

3
[ 123-75-1 ]
[ CAS Unavailable ]
[ 113845-68-4 ]

Yield	Reaction Conditions	Operation in experiment
93%	With bis(1,5-cyclooctadiene)nickel⁽⁰⁾; sodium t-butanolate; 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride In 1,4-dioxane at 80℃; for 3h; Inert atmosphere;
93%	With sodium t-butanolate In 1,4-dioxane at 80℃; for 3h; Inert atmosphere;	1.B Representative Procedure (coupling of phenylsulfamate 3, Table 1, entry 1) is used as an example). SI-3. A 20-mL reaction vial was charged with Ni(cod)2 (6.8 mg, 0.025 mmol, 5 mol%>), SIPr»HCl (21.2 mg, 0.05 mmol, 10 mol%>), anhydrous powdered NaOtBu (67.2 mg, 0.7 mmol, 1.4 equiv), and a magnetic stir bar, all in a glove box. Subsequently, a solution of sulfamate substrate 3 (100.5 mg, 0.50 mmol, 1 equiv) and morpholine (52.4 μ, 0.60 mmol, 1.2 equiv) in dioxane (2.5 mL) was added. The vessel was removed from the glove box, and then heated to 80 °C for 3 h. After cooling the reaction vessel to 23 °C and concentrating under reduced pressure, the crude residue was loaded onto a silica gel column (2.5 x 10 cm) and purified by flash chromatography (9: 1 Hexanes: Ethyl acetate) to yield aminated product SI-5 (78.1 mg, 95% yield) as a white solid. R/ 0.29 (9: 1 Hexanes :EtO Ac). Spectral data match those previously reported (Barker et al, J. Am. Chem. Soc. 2009, 131, 15598-15599). Any modifications of the conditions shown in this representative procedure are specified in the following schemes, which depict all of the results shown in Tables 1 and 2.; SI-29 (Table 2, entry 2). Purification by flash chromatography (20: 1 Hexanes:Et20) afforded aminated product SI-29 (93 %> yield) as a white solid. Spectral data match those previously reported (Brenner, E.; Schneider, R.; Fort, Y. Tetrahedron 1999, 55, 12829-12842).
90%	With (1,2-dimethoxyethane)dichloronickel(II); 2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole; sodium t-butanolate; 1,3-bis[(2,6-diisopropyl)phenyl]imidazolinium chloride In 1,4-dioxane at 23 - 80℃; for 4h; Inert atmosphere;

Reference： [1]Ramgren, Stephen D.; Silberstein, Amanda L.; Yang, Yang; Garg, Neil K. [Angewandte Chemie - International Edition, 2011, vol. 50, # 9, p. 2171 - 2173]
[2]Current Patent Assignee: UNIVERSITY OF CALIFORNIA - WO2012/94622, 2012, A2 Location in patent: Page/Page column 22-23; 27
[3]Hie, Liana; Ramgren, Stephen D.; Mesganaw, Tehetena; Garg, Neil K. [Organic Letters, 2012, vol. 14, # 16, p. 4182 - 4185]

4
[ 123-75-1 ]
[ 34857-71-1 ]
[ 113845-68-4 ]

Yield	Reaction Conditions	Operation in experiment
91%	With sodium t-butanolate In 1,4-dioxane at 80℃; for 3h; Inert atmosphere;	2.B Representative Procedure (coupling of phenylcarbamate SI-1, Table 3, entry 3) is used as an example). SI-7. A 20 mL reaction vial was charged with Ni(cod)2 (6.8 mg, 0.025 mmol, 5 mol%), SIPr'HCl (21.2 mg, 0.05 mmol, 10 mol%), anhydrous powdered NaOtBu (67.2 mg, 0.7 mmol, 1.4 equiv), and a magnetic stir bar, all in a glove box. Subsequently, a solution of carbamate substrate SI-1 (96.6 mg, 0.50 mmol, 1 equiv) and morpholine (52.4 μ,, 0.60 mmol, 1.2 equiv) in dioxane (2.5 mL) was added. The vessel was removed from the glove box, and then heated to 80 °C for 3 h. After cooling the reaction vessel to 23 °C and concentrating under reduced pressure, the crude residue was loaded onto a silica gel column (2.5 x 10 cm) and purified by flash chromatography (9: 1 Hexanes: EtOAc) to yield aminated product SI-7 (73.4 mg, 90% yield) as a white solid. R/ 0.29 (9: 1 Hexanes :EtO Ac). Spectral data match those previously reported (Barker, T. J.; Jarvo, E. R. J. Am. Chem. Soc. 2009, 131, 15598-15599). Any modifications of the conditions shown in this representative procedure are specified in the following schemes, which depict all of the results shown in Tables 3, 4, and 5.; SI-32 (Table 5, entry 2). Purification by flash chromatography (50: 1 Hexanes:Et20) afforded aminated product SI-32 (91%> yield) as a white solid. R 0.28 (50: 1 Hexanes:Et20). Spectral data match those previously reported (Brenner, E.; Schneider, R.; Fort, Y. Tetrahedron 1999, 55, 12829-12842).
86%	With (1,2-dimethoxyethane)dichloronickel(II); 2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole; sodium t-butanolate; 1,3-bis[(2,6-diisopropyl)phenyl]imidazolinium chloride In 1,4-dioxane at 23 - 80℃; for 4h; Inert atmosphere;

Reference： [1]Current Patent Assignee: UNIVERSITY OF CALIFORNIA - WO2012/94622, 2012, A2 Location in patent: Page/Page column 47; 52
[2]Hie, Liana; Ramgren, Stephen D.; Mesganaw, Tehetena; Garg, Neil K. [Organic Letters, 2012, vol. 14, # 16, p. 4182 - 4185]

5
[ 123-75-1 ]
[ 402-44-8 ]
[ 113845-68-4 ]

Yield	Reaction Conditions	Operation in experiment
95%	With bis(1,5-cyclooctadiene)nickel ⁽⁰⁾; sodium t-butanolate; 1,3-bis[2,6-bis(1-methylethyl)phenyl]-1,3-dihydro-2H-imidazol-2-ylidene monohydrochloride In toluene at 100℃; for 20h; Inert atmosphere; Schlenk technique;

Reference： [1]Zhu, Feng; Wang, Zhong-Xia [Advanced Synthesis and Catalysis, 2013, vol. 355, # 18, p. 3694 - 3702]

6
[ 123-75-1 ]
[ 1246260-87-6 ]
[ 113845-68-4 ]

Yield	Reaction Conditions	Operation in experiment
85%	With bis(1,5-cyclooctadiene)nickel ⁽⁰⁾; N,N′-bis(2,6-diisopropylphenyl)imidazol-2-ylidene hydrochloride; sodium t-butanolate In 1,4-dioxane at 75℃; for 5h; Molecular sieve; Schlenk technique;

Reference： [1]Zhang, Xue-Qi; Wang, Zhong-Xia [Organic and Biomolecular Chemistry, 2014, vol. 12, # 9, p. 1448 - 1453]

7
[ 123-75-1 ]
[ 455-13-0 ]
[ 113845-68-4 ]

Yield	Reaction Conditions	Operation in experiment
94%	With tripotassium phosphate tribasic; copper (I) iodide; N-((1-oxy-pyridin-2-yl)methyl)oxalamic acid In lithium hydroxide monohydrate; dimethyl sulfoxide at 25℃; Schlenk technique; Inert atmosphere; Sealed tube; chemoselective reaction;
82%	With {Ni(2,2'-bipyridine)3}Br₂; tetrabutylammonium bromide; 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl acetamide at 20℃; for 4h; Electrolysis; Inert atmosphere;
81%	With 1,1,3,3-tetramethylguanidine In acetonitrile for 24h; Inert atmosphere; Sealed tube; Sonication; Irradiation;

73%

With nickel(II) bromide ethylene glycol dimethyl ether; 4,4'-di-tert-butyl-2,2'-bipyridine; lithium bromide In 1,2-dimethoxyethane; N,N-dimethyl acetamide at 20℃; for 3h; Inert atmosphere; Electrochemical reaction;

Reference： [1]Wang, Yongbin; Ling, Jing; Zhang, Yu; Zhang, Ao; Yao, Qizheng [European Journal of Organic Chemistry, 2015, vol. 2015, # 19, p. 4153 - 4161]
[2]Kawamata, Yu; Vantourout, Julien C.; Hickey, David P.; Bai, Peng; Chen, Longrui; Hou, Qinglong; Qiao, Wenhua; Barman, Koushik; Edwards, Martin A.; Garrido-Castro, Alberto F.; Degruyter, Justine N.; Nakamura, Hugh; Knouse, Kyle; Qin, Chuanguang; Clay, Khalyd J.; Bao, Denghui; Li, Chao; Starr, Jeremy T.; Garcia-Irizarry, Carmen; Sach, Neal; White, Henry S.; Neurock, Matthew; Minteer, Shelley D.; Baran, Phil S. [Journal of the American Chemical Society, 2019, vol. 141, # 15, p. 6392 - 6402]
[3]Jati, Ayan; Dey, Kaushik; Nurhuda, Maryam; Addicoat, Matthew A.; Banerjee, Rahul; Maji, Biplab [Journal of the American Chemical Society, 2022, vol. 144, # 17, p. 7822 - 7833]
[4]Li, Chao; Kawamata, Yu; Nakamura, Hugh; Vantourout, Julien C.; Liu, Zhiqing; Hou, Qinglong; Bao, Denghui; Starr, Jeremy T.; Chen, Jinshan; Yan, Ming; Baran, Phil S. [Angewandte Chemie - International Edition, 2017, vol. 56, # 42, p. 13088 - 13093][Angew. Chem., 2017, vol. 129, p. 13268 - 13273,6]

8
[ 123-75-1 ]
[ 1263276-85-2 ]
[ 113845-68-4 ]

Yield	Reaction Conditions	Operation in experiment
83%	With (1,2-dimethoxyethane)dichloronickel(II); 2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole; sodium t-butanolate; 1,3-bis[(2,6-diisopropyl)phenyl]imidazolinium chloride In tert-butyl methyl ether at 80℃; for 3h; Green chemistry;

Reference： [1]Fine Nathel, Noah F.; Kim, Junyong; Hie, Liana; Jiang, Xingyu; Garg, Neil K. [ACS Catalysis, 2014, vol. 4, # 9, p. 3289 - 3293]

9
[ 92636-38-9 ]
[ 113845-68-4 ]

Yield	Reaction Conditions	Operation in experiment
40%	With carbon dioxide; Al⁽³⁺⁾*CF₃O₃S⁽²⁺⁾; hydrogen; tris(acetylacetonato)ruthenium(III); [2-((diphenylphospino)methyl)-2-methyl-1,3-propanediyl]bis[diphenylphosphine] In tetrahydrofuran at 160℃; for 16h;

Reference： [1]Li, Yuehui; Yan, Tao; Junge, Kathrin; Beller, Matthias [Angewandte Chemie - International Edition, 2014, vol. 53, # 39, p. 10476 - 10480][Angew. Chem., 2014, vol. 126, # 39, p. 10644 - 10648,5]

10
[ 615-18-9 ]
[ 113845-68-4 ]
[ 1637587-83-7 ]

Yield	Reaction Conditions	Operation in experiment
79%	With (4,4'-di-tert-butyl-2,2'-dipyridyl)-bis-(2-phenylpyridine(-1H))-iridium(III) hexafluorophosphate; sodium acetate In N,N-dimethyl acetamide; water at 20℃; Irradiation;

Reference： [1]Prier, Christopher K.; MacMillan, David W. C. [Chemical Science, 2014, vol. 5, # 11, p. 4173 - 4178]

11
[ 123-75-1 ]
[ CAS Unavailable ]
[ 113845-68-4 ]

Yield	Reaction Conditions	Operation in experiment
98%	With 1,4-diaza-bicyclo[2.2.2]octane; nickel(II) bromide dimethoxyethane; 6-(dimethylamino)-2,7-difluoro-9-mesityl-10-phenylacridin-10-ium-3-olate In N,N-dimethyl acetamide at -78 - 20℃; for 36h; Irradiation;
96%	Stage #1: pyrrolidine; p-trifluoromethylphenyl bromide With nickel(II) bromide dimethoxyethane; MTBD In N,N-dimethyl acetamide for 0.0333333h; Sonication; Stage #2: With 12,13,15,16-tetraphenyl-12,16-dihydroindeno[1,2-b]indeno[2’,1’:5,6]pyrido[3,2-g]quinoline In N,N-dimethyl acetamide at 20℃; for 36h; Irradiation;
95%	With 1,4-diaza-bicyclo[2.2.2]octane; nickel(II) bromide dimethoxyethane; tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate In dimethyl sulfoxide at 80℃; for 0.166667h; Flow reactor; Sealed tube; Schlenk technique; Inert atmosphere; Irradiation;

93%	With nickel(II) bromide trihydrate In N,N-dimethyl acetamide for 16h; Sealed tube; Irradiation;
91%	With 1,4-diaza-bicyclo[2.2.2]octane; tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; nickel(II) bromide trihydrate In dimethyl sulfoxide at 25 - 35℃; for 0.666667h; Irradiation; Flow reactor;
87%	With 1,4-diaza-bicyclo[2.2.2]octane; nickel(II) bromide dimethoxyethane; perixanthenoxanthene In N,N-dimethyl acetamide at 25℃; for 15h; Inert atmosphere; Irradiation; Schlenk technique; Sealed tube;
86%	With nickel(II) bromide dimethoxyethane; 4,4'-di-tert-butyl-2,2'-bipyridine; lithium bromide In 1,2-dimethoxyethane; N,N-dimethyl acetamide at 20℃; for 3h; Inert atmosphere; Electrochemical reaction;
86%	With nickel(II) bromide dimethoxyethane In N,N-dimethyl acetamide at 25℃; Inert atmosphere; Irradiation; Alkaline conditions; regiospecific reaction;
83%	Stage #1: pyrrolidine; p-trifluoromethylphenyl bromide With nickel(II) chloride hexahydrate; cadmium(II) sulphide In N,N-dimethyl acetamide for 0.00277778h; Schlenk technique; Sonication; Stage #2: In N,N-dimethyl acetamide at 20℃; for 24h; Schlenk technique; Irradiation;
80%	With 1,4-diaza-bicyclo[2.2.2]octane; nickel(II)bromide dimethoxyethane; 5,10-di(2-naphthyl)-5,10-dihydrophenazine In N,N-dimethyl acetamide at 20℃; for 24h; Inert atmosphere; Irradiation; Sealed tube;
80%	With 1,4-diaza-bicyclo[2.2.2]octane; nickel(II) bromide dimethoxyethane; 5,10-di(4-trifluoromethylphenyl)-5,10-dihydrophenazine In N,N-dimethyl acetamide at 25 - 60℃; for 24h; Irradiation;	8 General procedure: A dual photoredox/nickel catalytic approach employing 0.02 mol % of polypyridyl iridium PC [Ir{dF(CF)3ppy}2(dtbbpy)]PF6 [dF(CF3)ppy=2-(2,4-difluorophenyl)-5-(trifluoromethyl)pyridine; dtbbpy=4,4′-ditertbutyl-2,2′-bipyridine] in conjunction with NiBr2.glyme could efficiently catalyze C-N bond formation under mild reaction conditions. At similar reaction conditions, albeit using a higher catalyst loading (0.4 mol %), PC 5 or PC 7 in combination with NiBr2.glyme successfully catalyzed C-N coupling reactions at good to excellent yields (68% to 96%, FIG. 39). The scope of amines included both primary (aniline, furfurylamine, and propylamine) and secondary amines (pyrrolidine and morpholine) and were effectively coupled with electron-rich, electron-poor, and heter-ocyclic aryl bromides. For secondary amines, both PC 5 and 7 catalyzed C-N bond formations, although PC 5 generally gave slightly higher yields. Whilst PC 5 was unsuccessful in effecting C-N cross-coupling involving primary amines, PC 4 proved to be effective to couple primary amines in high yields.
77%	With nickel(II) bromide trihydrate In N,N-dimethyl acetamide at 20℃; for 3h; Sealed tube; Irradiation; Inert atmosphere;
71%	With 1,3-bis[(diphenylphosphino)propane]dichloronickel(II); 2-tert-butyl-1,1,3,3-tetramethylguanidine; 4-phenyl-N-methylpyridinium iodide; 4,4'-di-tert-butyl-2,2'-bipyridine; zinc In dimethyl sulfoxide at 60℃; for 8h; Inert atmosphere;
68%	With 1,4-diaza-bicyclo[2.2.2]octane; nickel(II) bromide dimethoxyethane; zinc In N,N-dimethyl acetamide at 20℃; for 18h; Inert atmosphere; Glovebox; Sealed tube;
62%	In N,N-dimethyl acetamide at 55℃; for 16h; Sealed tube; Glovebox; Irradiation;
54%	With Ni(bpy)<SUB>3</SUB>Br<SUB>2</SUB>; tetrabutylammomium bromide; 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl acetamide at 20℃; for 4h; Electrolysis; Inert atmosphere;
53%	With N,N,N,N-tetraethylammonium tetrafluoroborate In N,N-dimethyl-formamide; acetonitrile at 20℃; for 3.5h; Electrochemical reaction;
	With 1,4-diaza-bicyclo[2.2.2]octane; nickel(II) bromide dimethoxyethane In N,N-dimethyl acetamide at 20℃; for 20h; Irradiation;
	With 1,4-diaza-bicyclo[2.2.2]octane; tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; nickel(II) bromide trihydrate In dimethyl sulfoxide Flow reactor; Irradiation; Large scale;
97 %Spectr.	With Quinuclidine In N,N-dimethyl acetamide at 55℃; Irradiation;
89 %	With 1,4-diaza-bicyclo[2.2.2]octane; (1,2-dimethoxyethane)dichloronickel(II); 2,4,6-tris(diphenylamino)-3,5-difluorobenzonitrile In N,N-dimethyl acetamide at 20℃; Sealed tube; Inert atmosphere; Irradiation;

Reference： [1]Hutskalova, Valeriia; Sparr, Christof [Organic Letters, 2021, vol. 23, # 13, p. 5143 - 5147]
[2]Huang, Hai; Wang, Danfeng; Zhu, Xiaolin [Chemical Communications, 2022, vol. 58, # 21, p. 3529 - 3532]
[3]Park, Boyoung Y.; Pirnot, Michael T.; Buchwald, Stephen L. [Journal of Organic Chemistry, 2020, vol. 85, # 5, p. 3234 - 3244]
[4]Traxler, Michael; Gisbertz, Sebastian; Pachfule, Pradip; Schmidt, Johannes; Roeser, Jérôme; Reischauer, Susanne; Rabeah, Jabor; Pieber, Bartholomäus; Thomas, Arne [Angewandte Chemie - International Edition, 2022, vol. 61, # 21][Angew. Chem., 2022, vol. 134, # 21]
[5]Corcoran, Emily B.; Lévesque, François; McMullen, Jonathan P.; Naber, John R.; Wismer, Michael K. [Angewandte Chemie - International Edition, 2020, vol. 59, # 29, p. 11964 - 11968][Angew. Chem., 2020, vol. 132, # 29, p. 12062 - 12066,5]
[6]Pezzetta, Cristofer; Folli, Andrea; Matuszewska, Oliwia; Murphy, Damien; Davidson, Robert W. M.; Bonifazi, Davide [Advanced Synthesis and Catalysis, 2021, vol. 363, # 20, p. 4740 - 4753]
[7]Li, Chao; Kawamata, Yu; Nakamura, Hugh; Vantourout, Julien C.; Liu, Zhiqing; Hou, Qinglong; Bao, Denghui; Starr, Jeremy T.; Chen, Jinshan; Yan, Ming; Baran, Phil S. [Angewandte Chemie - International Edition, 2017, vol. 56, # 42, p. 13088 - 13093][Angew. Chem., 2017, vol. 129, p. 13268 - 13273,6]
[8]Ghosh, Indrajit; Khamrai, Jagadish; Savateev, Aleksandr; Shlapakov, Nikita; Antonietti, Markus; König, Burkhard [Science, 2019, vol. 365, # 6451, p. 360 - 366]
[9]Liu, Yi-Yin; Liang, Dong; Lu, Liang-Qiu; Xiao, Wen-Jing [Chemical Communications, 2019, vol. 55, # 33, p. 4853 - 4856]
[10]Du, Ya; Pearson, Ryan M.; Lim, Chern-Hooi; Sartor, Steven M.; Ryan, Matthew D.; Yang, Haishen; Damrauer, Niels H.; Miyake, Garret M. [Chemistry - A European Journal, 2017, vol. 23, # 46, p. 10962 - 10968]
[11]Current Patent Assignee: UNIVERSITY OF COLORADO (SYSTEM); COLORADO STATE UNIVERSITY SYSTEM - US2018/237550, 2018, A1 Location in patent: Paragraph 0067-0068; 0218
[12]Lim, Chern-Hooi; Kudisch, Max; Liu, Bin; Miyake, Garret M. [Journal of the American Chemical Society, 2018, vol. 140, # 24, p. 7667 - 7673]
[13]Han, Dongyang; Li, Sasa; Xia, Siqi; Su, Mincong; Jin, Jian [Chemistry - A European Journal, 2020, vol. 26, # 54, p. 12349 - 12354]
[14]Nocera, Daniel G.; Qin, Yangzhong; Sun, Rui [Angewandte Chemie - International Edition, 2020, vol. 59, # 24, p. 9527 - 9533][Angew. Chem.]
[15]Borlinghaus, Niginia; Kaschel, Johannes; Klee, Johanna; Haller, Vanessa; Schetterl, Jasmin; Heitz, Stephanie; Lindner, Tanja; Dietrich, Justin D.; Braje, Wilfried M.; Jolit, Anais [Journal of Organic Chemistry, 2021, vol. 86, # 2, p. 1357 - 1370]
[16]Kawamata, Yu; Vantourout, Julien C.; Hickey, David P.; Bai, Peng; Chen, Longrui; Hou, Qinglong; Qiao, Wenhua; Barman, Koushik; Edwards, Martin A.; Garrido-Castro, Alberto F.; Degruyter, Justine N.; Nakamura, Hugh; Knouse, Kyle; Qin, Chuanguang; Clay, Khalyd J.; Bao, Denghui; Li, Chao; Starr, Jeremy T.; Garcia-Irizarry, Carmen; Sach, Neal; White, Henry S.; Neurock, Matthew; Minteer, Shelley D.; Baran, Phil S. [Journal of the American Chemical Society, 2019, vol. 141, # 15, p. 6392 - 6402]
[17]Daili, Farah; Sengmany, Stéphane; Léonel, Eric [European Journal of Organic Chemistry, 2021, vol. 2021, # 17, p. 2462 - 2469]
[18]Qin, Yangzhong; Martindale, Benjamin C. M.; Sun, Rui; Rieth, Adam J.; Nocera, Daniel G. [Chemical Science, 2020, vol. 11, # 28, p. 7456 - 7461]
[19]Lévesque, François; Di Maso, Michael J.; Narsimhan, Karthik; Wismer, Michael K.; Naber, John R. [Organic Process Research and Development, 2020, vol. 24, # 12, p. 2935 - 2940]
[20]Kwak, Minjoon; Bok, Jinsol; Lee, Byoung-Hoon; Kim, Jongchan; Seo, Youngran; Kim, Sumin; Choi, Hyunwoo; Ko, Wonjae; Hooch Antink, Wytse; Lee, Chan Woo; Yim, Guk Hee; Seung, Hyojin; Park, Chansul; Lee, Kug-Seung; Kim, Dae-Hyeong; Hyeon, Taeghwan; Yoo, Dongwon [Chemical Science, 2022, vol. 13, # 29, p. 8536 - 8542]
[21]Gandini, Tommaso; Dolcini, Luigi; Di Leo, Lorenzo; Fornara, Matthieu; Bossi, Alberto; Penconi, Marta; Dal Corso, Alberto; Gennari, Cesare; Pignataro, Luca [ChemCatChem, 2022, vol. 14, # 23]

12
[ CAS Unavailable ]
[ 113845-68-4 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
84%	With tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; pentafluoronitrobenzen; potassium acetate In dichloromethane at 35℃; for 96h; Inert atmosphere; Irradiation; diastereoselective reaction;

13
[ 110-52-1 ]
[ 455-14-1 ]
[ 113845-68-4 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 24h; Inert atmosphere;
	With potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 80℃; for 24h; Inert atmosphere;
	With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 24h;

With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 24h; Inert atmosphere;

Reference： [1]Xu, Guo-Qiang; Xu, Ji-Tao; Feng, Zhi-Tao; Liang, Hui; Wang, Zhu-Yin; Qin, Yong; Xu, Peng-Fei [Angewandte Chemie - International Edition, 2018, vol. 57, # 18, p. 5110 - 5114][Angew. Chem., 2018, vol. 130, # 18, p. 5204 - 5208,5]
[2]An, Xiao-De; Li, Xian-Jiang; Liu, Qing; Shao, Chang-Lun; Xiao, Jian; Yang, Shuo; Zhou, Lan [Organic Letters, 2020]
[3]Xiao, Teng-Fei; Zhang, Yi-Fan; Hou, Wen-Tao; Yan, Pen-Ji; Hai, Jun; Xu, Peng-Fei; Xu, Guo-Qiang [Organic Letters, 2021, vol. 23, # 22, p. 8942 - 8946]
[4]Yi, Ming-Jun; Xiao, Teng-Fei; Li, Wen-Hui; Zhang, Yi-Fan; Yan, Pen-Ji; Zhang, Baoxin; Xu, Peng-Fei; Xu, Guo-Qiang [Chemical Communications, 2021, vol. 57, # 97, p. 13158 - 13161]

14
[ 2393-23-9 ]
[ 188622-31-3 ]
[ 2334446-49-8 ]
[ 113845-68-4 ]