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Chemical Structure| 13041-79-7 Chemical Structure| 13041-79-7

Structure of 4-Cyanostilbene
CAS No.: 13041-79-7

Chemical Structure| 13041-79-7

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Product Details of [ 13041-79-7 ]

CAS No. :13041-79-7
Formula : C15H11N
M.W : 205.25
SMILES Code : N#CC1=CC=C(C=C1)/C=C/C2=CC=CC=C2
English Name :(E)-4-Styrylbenzonitrile
MDL No. :MFCD00489188
InChI Key :WQUHPLQCUQJSQW-VOTSOKGWSA-N
Pubchem ID :5375774

Safety of [ 13041-79-7 ]

Application In Synthesis of [ 13041-79-7 ]

* 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 [ 13041-79-7 ]

[ 13041-79-7 ] Synthesis Path-Downstream   1~14

  • 1
  • [ 13041-79-7 ]
  • [ 14064-68-7 ]
YieldReaction ConditionsOperation in experiment
54% With covalent organic framework constructed from melamine and 2,4,6-triformylphloroglucinol In N,N-dimethyl-formamide at 20℃; for 18h; Irradiation;
With 9,10-Dicyanoanthracene In acetonitrile Irradiation; quantum yield of stilbene isomerization;
In acetonitrile at 25℃; Irradiation;
With [IrCp*Cl(5,7-Me,Me-QO)] In acetonitrile at 20℃; Inert atmosphere; Irradiation;

  • 2
  • [ 14064-68-7 ]
  • [ 13041-79-7 ]
YieldReaction ConditionsOperation in experiment
81% With iodine In hexane for 1h; Reflux; Synthesis of 1-15: General procedure: To a solution of benzyl chloride (0.126 g, 1.00 mmol) in dry toluene (7 mL), was added triphenylphosphine (0.313 g, 1.20 mmol) at ambient temperature. The reaction mixture was allowed to reflux for 18 h under N2 atmosphere; during this time the Wittig salt precipitated out, it was filtered, washed and used for further reaction. To a solution of Wittig salt (0.08 g, 0.20 mmol) in CH2Cl2, was added NaOH solution (0.01 g, 0.25 mmol, 3 mL water) at ambient temperature. The solution turned orange red indicating the formation of Wittig ylide. To this solution was added benzaldehyde (0.018 g, 0.16 mmol) and the reaction mixture allowed to stir at ambient temperature for 3 h. The crude product formed was extracted with CH2Cl2, washed with brine and evaporated to dryness. After usual column chromatography (hexane: EtOAc; 9:1), the product obtained was a mixture of cis and trans-isomer, isolated in 87% yield. The above mixture was dissolved in hexane containing catalytic amount of iodine and allowed to reflux for 1 h. The reaction mixture was cooled down to ambient temperature, washed with Na2S2O5 solution and the organic layer evaporated to give pure trans-isomer (1) in quantitative yield (89%)
With 9,10-Dicyanoanthracene In acetonitrile Irradiation;
  • 3
  • [ 100-52-7 ]
  • [ 104-85-8 ]
  • [ 13041-79-7 ]
YieldReaction ConditionsOperation in experiment
70% With tris(trimethylsilyl)amine; cesium fluoride In N,N-dimethyl-formamide at 50℃; for 24h; Inert atmosphere; Glovebox; Sealed tube;
29% With aluminum oxide; cesium fluoride In N,N-dimethyl-formamide for 4h; Heating;
  • 4
  • [ 9003-53-6 ]
  • [ 623-03-0 ]
  • [ 13041-79-7 ]
YieldReaction ConditionsOperation in experiment
99% With tetrakis[μ-1-[(3-methoxyphenyl)methyl]-2-phenyl-3-[2-oxo-2-[(2-phenolato-kO)aminokN]ethyl]-1H-imidazoliumato-kC4]tetrapalladium; tetrabutylammomium bromide; sodium acetate at 140℃; for 2h;
99% With tetrabutylammomium bromide; sodium acetate; C84H60N12O8Pd4 at 140℃; for 2h; Inert atmosphere; Schlenk technique;
98% With tetrabutylammonium acetate; palladium diacetate; DavePhos In 1,4-dioxane at 80℃; for 24h; Inert atmosphere; Sealed tube;
96% With tetrabutylammomium bromide; potassium carbonate In N,N-dimethyl-formamide at 100℃; for 24h; Inert atmosphere;
94% With C27H21F3N6OPd; tetrabutylammomium bromide; sodium acetate at 140℃; for 1h; Inert atmosphere;
93% With tetrabutylammomium bromide; sodium acetate In N,N-dimethyl acetamide at 135℃; for 10h;
93% With caesium carbonate; [{(PdCl)2}{{(o-PPh2)C6H4}C(O)N(C12H18)}2-K2-P,N] In N,N-dimethyl-formamide at 120℃;
91% With bis(η3-allyl-μ-chloropalladium(II)); tetrabutylammomium bromide; sodium carbonate In N,N-dimethyl acetamide at 120℃; for 24h; Inert atmosphere; diastereoselective reaction; 2.2. General procedure for the MH coupling reaction General procedure: 4-Nitrochlorobenzene (158 mg, 1 mmol), Na2CO3 (212 mg, 2 mmol), and n-Bu4NBr (240 mg, 0.75 mmol) were added into a dried schlenk tube with a magnetic bar, and then styrene (150 mL, 1.5 mmol), the solution of [Pd(C3H5)Cl]2 (100 mL, 0.0005 mmol) in DMA (3 mL) were added successively into it. The reaction mixture was heated in 120 °C for 4 h with stirring. After the reaction mixture was cooled to room temperature, water (4 mL) was added into it. The mixture solution was extracted with ethyl acetate (3 x 5 mL). The organic phase was washed with brine (3 x 5 mL) and dried with anhydrous Mg2SO4. The dried solution was filtered and evaporated under vacuum to give the crude product. The product was purified by silica gel chromatography (petroleum ether).
91% With C32H27N4O2Pd(1+)*BF4(1-); sodium acetate at 140℃; for 2h; Inert atmosphere; Schlenk technique;
90% With potassium carbonate In N,N-dimethyl acetamide at 130℃; for 24h;
89% With {4-[di(2-hydroxyethyl)amino]butyl}tri(n-butyl)ammonium bromide; palladium diacetate at 100℃; for 6h; Inert atmosphere; stereoselective reaction;
89% With C34H26Cl2N10Pd; tetrabutylammomium bromide; sodium acetate at 120℃; for 24h; 4.16. General procedure for H-MCR of aryl chlorides with styreneand methyl acrylate General procedure: To a 25mL RB flask was taken styrene (145.8 mg, 1.4 mmol) or methyl acrylate (120.5 mg, 1.4 mmol), aryl chloride (1.0 mmol),sodium acetate (90.2 mg, 1.1 mmol), TBAB (2.0 gm, 6.2 mol) and thecatalyst (4.0 mg, 0.005 mmol). The reaction mixture was heated to120 °C and stirred at the same temperature for 24 h and cooled. Theorganic portion from the reaction mixture was extracted withdiethyl ether (2 15 mL). The extracts were combined and thevolatiles removed on a rotavapor. The desired coupling product was isolated on a silica gel column using n-hexane/ethyl acetate/nhexane(2/98, v/v) mixture as eluent.
87% With potassium carbonate In N,N-dimethyl-formamide at 120℃; for 12h; Inert atmosphere;
84% With tris-(dibenzylideneacetone)dipalladium(0); bis(tri-t-butylphosphine)palladium(0); N-Methyldicyclohexylamine In toluene at 20℃; for 72h; Inert atmosphere;
78.5% With potassium carbonate In 1-methyl-pyrrolidin-2-one at 140℃; for 20h;
76% With [Gmim]Cl-Fe(III); triethylamine In neat (no solvent) at 80℃; for 12h; 2.3. Procedure for Heck reaction General procedure: In a 100 mL conical flask, a mixture of substituted haloben- zene (1 mmol), styrene (1.2 mmol), triethylamine (2 mmol) and [ Gmim ]Cl-Fe (III) (0.005 mol %) was added and stirred at 80 °C for a period as indicated in Table 4 (The reaction was monitored by HPLC and TLC). The resulting heterogeneous mixture was extracted with ethyl acetate or diethyl ether (3 ×5 mL). The organic phase was separated and dried over anhydrous Na 2 SO 4 and evaporated. The resulting crude was purified by column chromatography to give the desired pure product with excellent yield.
75.7% With tetrabutylammomium bromide; sodium acetate In 1-methyl-pyrrolidin-2-one at 130 - 150℃; for 24h;
73.4% With tetrabutylammomium bromide; sodium acetate In 1-methyl-pyrrolidin-2-one at 140℃; for 24h;
73% With tetrabutylammomium bromide; triethylamine In water; N,N-dimethyl-formamide at 110℃; for 7h; Green chemistry;
71% With triethylamine In N,N-dimethyl-formamide at 80℃; for 4h; stereoselective reaction; General procedure for Mizoroki-Heck coupling reaction General procedure: A mixture of aryl halide (1.0 mmol), alkene (1.1 mmol), triethylamine (2 mmol), DMF (5 mL), and the catalyst (30 mg, 0.28 mol% Pd ) was stirred at 80 °C for an appropriate time under aerial condition. The progress of the reaction was monitored by TLC. After completion of the reaction, the mixture was cooled to room temperature, poured into H2O (10 mL), and the catalyst was separated by magnetic decantation. In the case of acrylic acid, aqueous solution of Na2CO3 (10 mL, 3% w/v) was added; after separation of the catalyst, and the product was extracted with ethyl acetate (3 × 10 mL). The combined organic extracts were washed with brine (2 × 10 mL), dried over MgSO4, and concentrated in vacuum. The crude product was further purified by column chromatography (silica mesh size 60-120).
68% With tetrabutylammomium bromide; triethylamine In N,N-dimethyl-formamide at 130℃; for 24h; 6 2.3 General procedure for Mizoroki-Heck coupling reaction of aryl halides with olefins General procedure: To a 25 mL round bottom flask containing aryl halide (1 mmol), olefin (1.2mmol), Et3N (1.5mmol), and ZnO nanoplates supported hydrazone-based palladacycle (10mg, 0.26 mol% Pd), 3mL DMF was added as solvent. The resulting solution was stirred at 130°C in an oil bath. The reaction was followed by TLC (thin layer chromatography) and at the end; it was allowed to cool to room temperature and was centrifuged to separate the catalyst. The residue was diluted with ethyl acetate (2×5mL), and washed with water (2×5mL). Then the organic phase was dried with anhydrous MgSO4, filtered, and the solvent was removed by evaporation under vacuum conditions. Further purification was achieved by thin layer chromatography plate, using EtOAc and n-hexane with 2:10 ratio as eluent.
66% With (1,4,10,13-tetraoxa-7,16-diazacyclooctadecane)palladium(II) chloride; tetrabutylammomium bromide; triethylamine In N,N-dimethyl-formamide at 130℃; for 4h; Aralkenes 3; General Procedure General procedure: A 5 mL round-bottomed flask was charged with aryl halide 1 (1 mmol), alkene 2 (1.1 mmol), PdCl2-cryptand 22 (0.009 mmol, 0.9 mol%), Et3N (1.1 mmol), and DMF (1 mL). [For aryl bromides or chlorides, TBAB (1 mmol) was also added]. The mixture was stirred at 130 °C for the appropriate time (Table 2) while the progress of the reaction was monitored (TLC). Upon completion of the reaction, the mixture was cooled to r.t., poured into H2O (10 mL), and extracted with CH2Cl2 (3 × 8 mL). The combined organic extracts were washed with brine (2 × 8 mL), dried (MgSO4), and concentrated. Purification by preparative TLC [silica gel, hexane or hexane-EtOAc (9:1)] gave the pure product.
62% With potassium phosphate; C24H22ClN3OPdSe; tetrabutylammomium bromide In water at 110℃; for 12h;
58% With tetrabutylammomium bromide; sodium acetate In 1-methyl-pyrrolidin-2-one at 140 - 150℃;
58% In various solvent(s) at 100℃; for 10h;
58% With C26H28Cl2N2O5Pd*H2O; tetrabutylammomium bromide; triethylamine In N,N-dimethyl-formamide at 130℃; for 2h;
48% With tetrabutylammomium bromide; sodium acetate In N,N-dimethyl acetamide for 68h;
45% With C5H11Br2N4Pd; sodium acetate In 1-methyl-pyrrolidin-2-one at 120℃; for 24h; Inert atmosphere;
95 % Chromat. With Pd(Et2S)2Cl2; tetrabutylammomium bromide; sodium acetate In N,N-dimethyl acetamide at 120℃; for 92h;
With sodium hydroxide In N,N-dimethyl-formamide at 150℃; for 3h; Sealed tube;
With tetrabutylammonium nitrate; sodium hydroxide; palladium dichloride at 120℃; for 24h; General procedure for Heck reaction in the presenceof PdCl2/n-Bu4NNO3 General procedure: A mixture of tetrabutylammonium nitrate (0.5 mmol,0.15 g), aryl halide (1.0 mmol), n-butyl acrylate or styrene (2.0 mmol), PdCl2 (0.03 mmol, 0.0053 g), and NaOH(2.0 mmol, 0.08 g) were added to a flask. The mixture washeated in an oil bath at 120 °C with stirring and the reactionwas followed by TLC analysis. When the reaction was completed,the solution was allowed to cool to room temperatureand the product was extracted with diethyl ether (3 × 3 mL).The solvent was then removed and the pure product wasobtained by chromatography over a short column of silicagel using n-hexane/ethyl acetate (4:1) as the eluent.
75 % With caesium carbonate; (Z)-2-ethoxy-3-((p-tolylamino)methylene)chroman-4-one; palladium dichloride In water at 90℃;
99 % With tetrabutylammomium bromide; sodium acetate; C19H26ClN2OPPd at 140℃; Schlenk technique; Inert atmosphere;

References: [1]Lee, Jhen-Yi; Su, Yong-Siang; Wang, Yu-Shan; Lee, Hon Man [Advanced Synthesis and Catalysis, 2019, vol. 361, # 20, p. 4714 - 4726].
[2]Hung, Cheng-Hau; Zheng, Wei-Yuan; Lee, Hon Man [Organometallics, 2021, vol. 40, # 6, p. 702 - 713].
[3]Location in patent: experimental part Xu, Hua-Jian; Zhao, Yong-Qiang; Zhou, Xin-Feng [Journal of Organic Chemistry, 2011, vol. 76, # 19, p. 8036 - 8041].
[4]Chen, Liyu; Rangan, Sylvie; Li, Jing; Jiang, Huanfeng; Li, Yingwei [Green Chemistry, 2014, vol. 16, # 8, p. 3978 - 3985].
[5]Location in patent: experimental part Sie, Ming-Han; Hsieh, Yuan-Hsin; Tsai, Yi-Hua; Wu, Jia-Rong; Chen, Shih-Jung; Kumar, P. Vijaya; Lii, Jenn-Huei; Lee, Hon Man [Organometallics, 2010, vol. 29, # 23, p. 6473 - 6481].
[6]Kantam, M. Lakshmi; Roy, Sarabindu; Roy, Moumita; Subhas; Likhar, Pravin R.; Sreedhar, Bojja; Choudary [Synlett, 2006, # 17, p. 2747 - 2750].
[7]Sabharwal, Gazal; Dwivedi, Khilesh C.; Balakrishna, Maravanji S. [Dalton Transactions, 2025, vol. 54, # 30, p. 11551 - 11562].
[8]Location in patent: experimental part Wang, Wei; Yang, Qin; Zhou, Rong; Fu, Hai-Yan; Li, Rui-Xiang; Chen, Hua; Li, Xian-Jun [Journal of Organometallic Chemistry, 2012, vol. 697, # 1, p. 1 - 5].
[9]Lo, Chi Hou; Lee, Hon Man [Organometallics, 2018, vol. 37, # 7, p. 1150 - 1159].
[10]Li, Hongji; Wang, Lei; Li, Pinhua [Synthesis, 2007, # 11, p. 1635 - 1642].
[11]Location in patent: experimental part Wang, Lei; Li, Hongji; Li, Pinhua [Tetrahedron, 2009, vol. 65, # 1, p. 364 - 368].
[12]Mishra, Vishwesh; Thomas, Jisha Mary; Chinnappan, Sivasankar; Thirupathi, Natesan [Journal of Organometallic Chemistry, 2019, vol. 892, p. 1 - 17].
[13]Panahi, Farhad; Zarnaghash, Narges; Khalafi-Nezhad, Ali [New Journal of Chemistry, 2016, vol. 40, # 2, p. 1250 - 1255].
[14]Littke, Adam F.; Fu, Gregory C.; Ober, Michael H.; Denmark, Scott E. [Organic Syntheses, 2005, vol. 81, p. 63 - 76].
[15]Iyer, Suresh; Kulkarni, Girish M.; Ramesh; Sattar, Aruna K. [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2005, vol. 44, # 9, p. 1894 - 1908].
[16]Deepa, Manickam; Selvarasu, Uthayanila; Kalaivani, Kolanjinathan; Parasuraman, Karthikeyan [Journal of Organometallic Chemistry, 2021, vol. 954-955].
[17]Iyer, Suresh; Jayanthi [Synlett, 2003, # 8, p. 1125 - 1128].
[18]Iyer, Suresh; Kulkarni, Girish M.; Ramesh [Tetrahedron, 2004, vol. 60, # 9, p. 2163 - 2172].
[19]Movassagh, Barahman; Rezaei, Nasrin [New Journal of Chemistry, 2015, vol. 39, # 10, p. 7988 - 7997].
[20]Vibhute, Sandip P.; Mhaldar, Pradeep M.; Shejwal, Rajendra V.; Rashinkar, Gajanan S.; Pore, Dattaprasad M. [Tetrahedron Letters, 2020, vol. 61, # 17].
[21]Nouri, Fatemeh; Rostamizadeh, Shahnaz; Azad, Mohammad [Inorganica Chimica Acta, 2018, vol. 471, p. 664 - 673].
[22]Movassagh, Barahman; Yasham, Shahriar; Navidi, Mozhgan [Synlett, 2013, vol. 24, # 20, p. 2671 - 2674].
[23]Sharma, Kamal Nayan; Satrawala, Naveen; Srivastava, Avinash Kumar; Ali, Munsaf; Joshi, Raj Kumar [Organic and Biomolecular Chemistry, 2019, vol. 17, # 40, p. 8969 - 8976].
[24]Iyer, Suresh; Jayanthi, A [Tetrahedron Letters, 2001, vol. 42, # 44, p. 7877 - 7878].
[25]Hong, Ji Li; Wang, Lei [European Journal of Organic Chemistry, 2006, # 22, p. 5099 - 5102].
[26]Movassagh, Barahman; Ranjbari, Shabnam [Applied Organometallic Chemistry, 2018, vol. 32, # 4].
[27]Herrmann, Wolfgang A.; Brossmer, Christoph; Reisinger, Claus-Peter; Riermeier, Thomas H.; Oefele, Karl; Beller, Matthias [Chemistry - A European Journal, 1997, vol. 3, # 8, p. 1357 - 1364].
[28]Owusu, Millicent O.; Handa, Sachin; Slaughter, Legrande M. [Applied Organometallic Chemistry, 2012, vol. 26, # 12, p. 712 - 717].
[29]Gruber, Adriane S; Pozebon, Dirce; Monteiro, Adriano L; Dupont, Jarton [Tetrahedron Letters, 2001, vol. 42, # 42, p. 7345 - 7348].
[30]Donga, Zhongmin; Yea, Zhibin [Advanced Synthesis and Catalysis, 2014, vol. 356, # 16, p. 3401 - 3414].
[31]Nowrouzi, Najmeh; Tarokh, Dariush [Journal of the Iranian Chemical Society, 2015, vol. 12, # 9, p. 1623 - 1628].
[32]Khan, Danish; Parveen, Iram [European Journal of Organic Chemistry, 2021, vol. 2021, # 35, p. 4946 - 4957].
[33]Kao, Cheng-Po; Lee, Jhen-Yi; Tang, Min-Cheng; Lee, Hon Man [Dalton Transactions, 2024, vol. 53, # 25, p. 10475 - 10485].
  • 5
  • [ 9003-53-6 ]
  • [ 623-00-7 ]
  • [ 13041-79-7 ]
YieldReaction ConditionsOperation in experiment
99% With sodium acetate In N,N-dimethyl acetamide at 140℃; for 20h;
99% With C34H26Cl2N10Pd; tetrabutylammomium bromide; sodium acetate at 120℃; for 12h; 4.15. General procedure for H-MCR of aryl bromides with styrene General procedure: To a 25mL RB flask was taken styrene (145.8 mg, 1.4 mmol), arylbromide (1.0 mmol), sodium acetate (90.2 mg, 1.1 mmol), TBAB(2.0 gm, 6.2 mol) and the catalyst (0.8 mg, 0.001 mmol). The reactionmixture was heated to 120 °C and stirred at the same temperaturefor 12 h and cooled. The organic portion from the reactionmixture was extracted with diethyl ether (2 15 mL). The extractswere combined and the volatiles removed on a rotavapor. Thedesired coupling product was isolated on a silica gel column usingn-hexane/ethyl acetate/n-hexane (2/98, v/v) mixture as eluent.
98% With 3-(dimethylamino)propanoic acid hydrochloride; potassium carbonate In 1-methyl-pyrrolidin-2-one at 130℃; for 10h;
98% With aluminum oxide; potassium phosphate for 0.333333h; microwave irradiation;
98% With bis(η3-allyl-μ-chloropalladium(II)); tetrabutylammomium bromide; sodium acetate In N,N-dimethyl acetamide at 130℃; for 24h; Inert atmosphere; optical yield given as %de; diastereoselective reaction; 2.2. General procedure for the MH coupling reaction General procedure: 4-Nitrochlorobenzene (158 mg, 1 mmol), Na2CO3 (212 mg, 2 mmol), and n-Bu4NBr (240 mg, 0.75 mmol) were added into a dried schlenk tube with a magnetic bar, and then styrene (150 mL, 1.5 mmol), the solution of [Pd(C3H5)Cl]2 (100 mL, 0.0005 mmol) in DMA (3 mL) were added successively into it. The reaction mixture was heated in 120 °C for 4 h with stirring. After the reaction mixture was cooled to room temperature, water (4 mL) was added into it. The mixture solution was extracted with ethyl acetate (3 x 5 mL). The organic phase was washed with brine (3 x 5 mL) and dried with anhydrous Mg2SO4. The dried solution was filtered and evaporated under vacuum to give the crude product. The product was purified by silica gel chromatography (petroleum ether).
98% With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 3h; Inert atmosphere; 4.4 General Procedure for the Heck Coupling Reaction General procedure: The aryl halide (2mmol), olefin (3mmol), K2CO3(3mmol)and the catalyst (TMP-PECH-Amine G1-Pd) were taken ina 50mL RB flask and DMF was added as solvent. The reactionmixture was stirred at 80°C under a nitrogen atmosphere.The progress of the reaction was monitored by thinlayerchromatography (TLC). After completion, the reactionmixture was cooled, distilled water was added to the reaction mixture, and extracted with diethyl ether (3 × 10mL). Theorganic phase was washed several times with water and driedover anhydrous MgSO4.After evaporation of the solvent, thepure product was obtained in high yield. The isolated productswere characterized by GCMS, 1H NMR and 13C NMR.
97% With C5H11Br2N4Pd; sodium acetate In 1-methyl-pyrrolidin-2-one at 120℃; for 24h; Inert atmosphere;
97% With triethylamine In N,N-dimethyl-formamide at 120℃; for 6h;
97% With triethylamine In N,N-dimethyl-formamide at 120℃; for 6h; stereoselective reaction;
97% With potassium carbonate In methanol; water at 45℃; for 6h; Green chemistry; stereoselective reaction; General procedure for Heck reaction General procedure: In the typical procedure for Heck coupling reaction, a mixture of iodobenzene (1 mmol), styrene (2 mmol), K2CO3 (5 mmol), and catalyst (0.14 g, Pd-MPVP) in MeOH/H2O (volume ratio: 3:1) (5 mL) was placed in a round bottom flask. The suspension was stirred at 45 °C for 4 h. The progress of reaction was monitored by TLC using n-hexane as eluent. After completion of the reaction (monitored by TLC), for the reaction work-up, the catalyst was removed from the reaction mixture by filtration, and then the reaction product was extracted with CH2Cl2 (3 mL 5 mL). The solvent was removed under reduced pressure. The crude product was purified by flash column chromatography to afford the desired coupling product (97% isolated yield). The product was identified with 1H NMR, 13C NMR and FT-IR spectroscopy techniques.
96% With phenyl carbamate; potassium carbonate In N,N-dimethyl-formamide at 130℃; for 2h;
96% With [NBu4][Pd(DMSO)Cl3]; tetrabutyl-ammonium chloride; sodium acetate In N,N-dimethyl acetamide at 140℃; for 6h;
95% In various solvent(s) at 100℃; for 10h;
95% With {4-[di(2-hydroxyethyl)amino]butyl}tri(n-butyl)ammonium bromide; palladium diacetate at 100℃; for 6h; Inert atmosphere; stereoselective reaction;
95% With sodium carbonate In N,N-dimethyl-formamide at 140℃; for 24h; Inert atmosphere;
95% With tetrabutylammomium bromide; triethylamine In N,N-dimethyl-formamide at 130℃; for 1h; 1 2.3 General procedure for Mizoroki-Heck coupling reaction of aryl halides with olefins General procedure: To a 25 mL round bottom flask containing aryl halide (1 mmol), olefin (1.2mmol), Et3N (1.5mmol), and ZnO nanoplates supported hydrazone-based palladacycle (10mg, 0.26 mol% Pd), 3mL DMF was added as solvent. The resulting solution was stirred at 130°C in an oil bath. The reaction was followed by TLC (thin layer chromatography) and at the end; it was allowed to cool to room temperature and was centrifuged to separate the catalyst. The residue was diluted with ethyl acetate (2×5mL), and washed with water (2×5mL). Then the organic phase was dried with anhydrous MgSO4, filtered, and the solvent was removed by evaporation under vacuum conditions. Further purification was achieved by thin layer chromatography plate, using EtOAc and n-hexane with 2:10 ratio as eluent. 2.3.1 Selected spectral data of the Mizoroki-Heck products RRN 23,25,27,29,31,33,35,37,39,412.3.1.1 24 (E)-4-styrylbenzonitrile (6a, 6g) (0010) δH (300MHz; CDCl3; Me4Si): 7.09 (3J=18.25, 1H, d, CH), 7.22 (3J=18.25, 1H, d, CH), 7.32 (1H, dd, CH), 7.39 (2H, dd, CH), 7.54 (3J=8.2, 2H, d, CH), 7.57 (3J=7.4, 2H, d, CH), 7.64 (3J=7.4, 2H, d, CH); δC (75MHz; CDCl3; Me4Si): 110.5, 119.03, 126.7, 126.8, 126.9, 128.6, 128.8, 132.4, 132.4, 136.2, 141.8.
94% With tributyl-amine; polymer-bound dichloropalladium di(pyrid-2-yl)amide In N,N-dimethyl-formamide at 140℃; for 90h;
94% With potassium carbonate In N,N-dimethyl acetamide at 130℃; for 12h;
94% With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 10h;
94% With [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene](3-chloropyridyl)palladium(II) dichloride; caesium carbonate In neat (no solvent) at 100℃; for 12h; 4.2. General procedure for Heck Cross-Coupling reactions General procedure: To a single-necked flask (15 mL) equipped with a stir bar charge with 1 (1 eq, 1 mmol), 2 (1 eq, 1.2 mmol), NHC-Pd (II)-Py (0.01 eq, 0.06 g) and Cs2CO3 (0.3 eq, 0.1 g). Then the reaction flask was stirred at 100 °C for 12 h, and then the reaction mixture was cooled to room temperature. After removing the solvent under reduced pressure, the pure product was obtained by silica gel column chromatography (eluent: petroleum ether/ethyl acetate).
93% With sodium carbonate In N,N-dimethyl acetamide; water at 130℃; for 2h;
93% With 1-butyl-3-methylimidazolium lactate; palladium; triethylamine In water; N,N-dimethyl-formamide at 90℃; for 9h; Green chemistry;
93% With [Pd2(dppe)2(S(C6H4)S)]2*(OTf)4; tetrabutylammomium bromide; sodium acetate In N,N-dimethyl acetamide; water at 120℃; for 16h; Inert atmosphere; Typical experimental procedure General procedure: In an oven dried 25 ml Schlenk tube was charged with DMA (3 mL), aryl bromide (1 mmol), styrene (1.5 mmol), aqueous NaOAc (2 mmol, 1 mL) and catalyst (0.4 mol%). The reactants were heated at 120 °C with stirring for 16 h under a nitrogen atmosphere. The reaction mixture was cooled to room temperature, the contents were diluted with water(5 mL), neutralized with dil HCl and extracted with ethyl acetate (3 x 20 mL). The whole organic extract was washed with water (2 x 15 mL), dried over anhydrous Na2SO4, filtered and the solvent was removed under reduced pressure. The residue was characterized by NMR spectra.
93% With cetyltrimethylammonim bromide; potassium carbonate; (+)-sodium L-ascorbate In water; N,N-dimethyl-formamide at 100℃; for 10h; Inert atmosphere; Schlenk technique;
93% With N,N-dimethylammonium chloride; potassium carbonate In glycerol at 100℃; for 7h; Typical method for the Heck coupling reaction General procedure: To a mixture of aryl halide (1 mmol), alkene (1.2 mmol), and K2CO3 (2 mmol) in DES (DMAC:Gly, 3 mL), 0.018 g of GO-Fe3O4-Cellulose-Pd (0.75 mol%) was added. The mixture was stirred at 100 °C and the progress of reaction was checked by thin layer chromatography (TLC). The mixture was quenched with water (15 mL) after completing the reaction, and extracted with ethyl acetate (3 × 10 mL). The organic extract was dried over Na2SO4 and concentrated under vacuum. Purification of the obtained crude product was performed by column chromatography on silica gel. The aqueous phase, which contained both of the catalyst and DES, was used for another run after evaporation of water.
92% With CF3O3S(1-)*C52H46NO2P2Pd(1+); potassium carbonate In 1-methyl-pyrrolidin-2-one at 130℃; for 0.3h; In air; Microwave irradiation; chemoselective reaction;
92% With [Pd{C6H4(CH2N(CH2Ph)2)(μ-Br)}]2; potassium carbonate In 1-methyl-pyrrolidin-2-one at 130℃; for 1.16667h; 3.2. General procedure for Heck cross-coupling reaction General procedure: In a round-bottom flask equipped with a magnetic stirring bar to a mixture of K2CO3 (1.1 mmol), olefin (2.2 mmol) and aryl halide (1 mmol) in NMP (3 ml) were added 0.1 mol% of palladacycle complex (A) and equipped with a condenser for refluxing. The above mixture was heated at 130 °C in an oil bath. The reaction's progress was monitored by TLC (hexane/EtOAc, 80:20) and gas chromatography (GC). After completion of the reaction the mixturewas diluted with n-hexane and water. The organic layer was washed with brine, dried over Na2SO4, and concentrated under reduced pressure. The residue was purified by recrystallization from ethanol and water. The products were characterized by comparing their m.p., IR, 1H, 13C NMR spectra with those found in the literature [41-43].
92% With [Pd{C6H2-(CH2CH2NH2)-(OMe)2-3,4}Br(PPh3)]; potassium carbonate In 1-methyl-pyrrolidin-2-one at 130℃; for 1.66667h; General procedure for Heck reactions of aryl halides with olefins General procedure: To a round-bottom flask equipped with a magnetic stirring bar were added monomeric palladacycle 2 (0.4 mol %), K2CO3 (1.1 mmol), olefin (2.2 mmol) and aryl halide (1 mmol) in NMP (3 mL). The mixture was heated at 130 °C using an oil bath and the progress was monitored by TLC (hexane/EtOAc, 80:20) and gas chromatography (GC). After completing the reaction, the mixture was diluted with n-hexane (30 mL) and H2O. The organic layer was washed with brine (20 mL), dried over Na2SO4, and concentrated under reduced pressure. The residue was purified by recrystallization from EtOH and H2O. The products were characterized by comparing their mp and IR, 1H and 13C NMR spectra with those reported in the literature.
92% With caesium carbonate In water at 100℃; for 5h; Inert atmosphere;
92% With {Pd[C6H2(CH2CH2NH2)-(OMe)(2),3,4] (μ-Br)}2; sodium acetate at 130℃; for 0.3h; Microwave irradiation; Ionic liquid;
92% With sodium carbonate In N,N-dimethyl acetamide; water at 125℃; for 4h; Sealed tube;
92% With sodium acetate In N,N-dimethyl acetamide; water at 120℃; for 16h; Inert atmosphere;
91% With tetrabutylammomium bromide; potassium carbonate In N,N-dimethyl-formamide at 130℃; for 24h; 3.5 General Procedure fortheHeck Reaction ofArylElectrophiles inthePresence oftheNano-PdCatalyst General procedure: Styrene (1.4mmol) was added to a stirring mixture of arylhalide (1.0 mmol), K2CO3(1.5 mmol), nano-pd catalyst(1.5mol%), TBAB (0.5mmol) in DMF (3.0mL) and thenthe reaction mixture was heated at 130 °C for the appropriatetime. The mixture was cooled down to room temperatureand the catalyst was isolated using an externalmagnet. Then, the residue was diluted with H2O(10.0mL)and extracted with EtOAc (10 × 3). The combined organicphases were combined and dried over anhydrous Na2SO4.Concentration of the mixture and column chromatographyon silica gel afforded the desired cross-coupling productsin high yield.
91% With potassium carbonate In water; N,N-dimethyl-formamide at 70℃; for 3h; Inert atmosphere; General procedure for Mizoroki-Heck C-C coupling reactions General procedure: The potential activity of the newly prepared Pd/TATAE catalyst was analyzed in the Mizoroki-Heck cross-coupling reaction (Scheme 2). Aryl bromide (1 mmol), styrene (1.2 mmol), K2CO3 (1.2 mmol), and Pd/TATAE (20 mg) were taken in dimethylformamide (DMF)/water mixture (1:2 ratio, 2 mL), and the mixture was stirred at 70 °C for about 3 h. After reaction completion (monitored by TLC), the reaction mixture was diluted with 5 mL ethyl acetate, then the catalyst was removed by simple filtration using Whatman-40 filter paper. The filtrate was extracted with excess amount of ethyl acetate, then concentrated under reduced pressure. The crude product was further purified by silica gel (60-120 mesh) column chromatography (petroleum ether/ethyl acetate) to afford the corresponding products.
91% With potassium carbonate In N,N-dimethyl-formamide at 110℃; for 10h; Green chemistry; 2.4. General procedure for the Heck reaction catalyzed by PS-Pd-salencomplex General procedure: In general procedure, 30 mg of PS-Pd-salen complex 1f was added tothe mixture of iodobenzene (1 mmol, 0.204 g), styrene or the alkylacrylate (1.2 mmol), the base (2 mmol) in 5 mL of dimethyl formaldehydeand reaction mixture was heated at 110 °C for between 4and 20 h, depending on the reaction.
90% With potassium phosphate; tetrabutylammomium bromide In N,N-dimethyl-formamide at 140℃; for 24h;
90% With 2-aminophenyl diphenylphosphinite; tetrabutylammomium bromide; palladium diacetate; sodium hydroxide In water at 95℃; for 3.5h;
90% With tetrabutylammomium bromide; triethylamine In water; N,N-dimethyl-formamide at 110℃; for 4h; Green chemistry;
90% With potassium carbonate In N,N-dimethyl-formamide at 120℃; for 10h;
90% With triethylamine In N,N-dimethyl-formamide for 0.216667h; Sonication;
89% With 1-(3-aminopropyl)-3-methylimidazolium hexafluorophosphate; palladium; 3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate at 120℃; for 24h; Inert atmosphere; Ionic liquid; regioselective reaction;
89% With potassium carbonate In water; dimethyl sulfoxide at 90℃; for 10h; Green chemistry;
89% With glucosamine; palladium diacetate; potassium carbonate In water; N,N-dimethyl-formamide at 120℃; for 1h; Microwave irradiation; Green chemistry; General Experimental Procedure and Characterization Data for Representative Compounds General procedure: D-glucosamine (428 mg, 2.0 mmol) was dissolved in DMF-H2O(1:1, 2 mL). Styrene (0.214 mL, 2.0 mmol), aryl halide (2.0mmol), K2CO3 (3 equiv) and Pd(OAc)2 (1 mol%) were added to it,and the contents sealed in a vial were irradiated under microwaveirradiation at an output power of 100 W for 1 h at 120 °C.The reaction mixture was extracted with hexane (3 × 25mL).The combined organic layers were washed with H2O, dried overNa2SO4, filtered, and concentrated under reduced pressure.Column chromatography on silica gel afforded pure products.
89% With C21H21ClN4Pd; triethylamine In 1-methyl-pyrrolidin-2-one at 140℃; for 8h; Sealed tube;
88% With tributyl-amine In N,N-dimethyl-formamide at 140℃; for 90h;
88% With triethylamine at 80℃; for 10h;
88% With [K2(H2O)3{(H2O)0.5(at)decamethylcucurbit[5]uril}][PdCl4]; sodium carbonate In N,N-dimethyl-formamide at 140℃; for 24h;
88% With C26H28Cl2N2O5Pd*H2O; tetrabutylammomium bromide; triethylamine In N,N-dimethyl-formamide at 130℃; for 0.166667h;
87% With potassium carbonate In N,N-dimethyl-formamide at 130℃; for 30h;
87% With triethylamine In N,N-dimethyl-formamide at 100℃; for 2h; 2.5 General Procedure for Heck Coupling Reaction General procedure: A mixture of aryl halide (1 mmol), olefin (1.5 mmol), Et3N (2 mmol) and Pd-imino-Py-c-Fe2O3 (0.25 mol%, 0.009 g)was stirred at 100 °C in DMF (2 mL) for an appropriate time (Table 2). The catalyst was separated by an external magnet, washed with EtOH, dried and reused for a consecutive run under the same reaction conditions. Evaporation of the solvent of the filtrate under reduced pressure gave the crude products. The pure products were isolated by chromatography on silica gel eluted with n-hexane:EtOAc (50:1).

References: [1]Yao, Qingwei; Kinney, Elizabeth P.; Zheng, Chong [Organic Letters, 2004, vol. 6, # 17, p. 2997 - 2999].
[2]Mishra, Vishwesh; Thomas, Jisha Mary; Chinnappan, Sivasankar; Thirupathi, Natesan [Journal of Organometallic Chemistry, 2019, vol. 892, p. 1 - 17].
[3]Cui, Xin; Li, Zhe; Tao, Chuan-Zhou; Xu, Yu; Li, Juan; Liu, Lei; Guo, Qing-Xiang [Organic Letters, 2006, vol. 8, # 12, p. 2467 - 2470].
[4]Du, Li-Hua; Wang, Yan-Guang [Synthetic Communications, 2007, vol. 37, # 2, p. 217 - 222].
[5]Location in patent: experimental part Wang, Wei; Yang, Qin; Zhou, Rong; Fu, Hai-Yan; Li, Rui-Xiang; Chen, Hua; Li, Xian-Jun [Journal of Organometallic Chemistry, 2012, vol. 697, # 1, p. 1 - 5].
[6]Hiba; Krishna, G. Anjali; Prathapan; Sreekumar [Catalysis Letters, 2022, vol. 152, # 6, p. 1819 - 1834].
[7]Owusu, Millicent O.; Handa, Sachin; Slaughter, Legrande M. [Applied Organometallic Chemistry, 2012, vol. 26, # 12, p. 712 - 717].
[8]Huang, Yuanbiao; Gao, Shuiying; Liu, Tianfu; Lue, Jian; Lin, Xi; Li, Hongfang; Cao, Rong [ChemPlusChem, 2012, vol. 77, # 2, p. 106 - 112].
[9]Huang, Yuanbiao; Gao, Shuiying; Liu, Tianfu; Lue, Jian; Lin, Xi; Li, Hongfang; Cao, Rong [Collection of Czechoslovak Chemical Communications, 2012, vol. 77, # 2, p. 106 - 112].
[10]Kalbasi, Roozbeh Javad; Negahdari, Meysam [Journal of Molecular Structure, 2014, vol. 1063, # 1, p. 259 - 268].
[11]Cui, Xin; Zhou, Yuan; Wang, Na; Liu, Lei; Guo, Qing-Xiang [Tetrahedron Letters, 2007, vol. 48, # 1, p. 163 - 167].
[12]Schroeter, Felix; Soellner, Johannes; Strassner, Thomas [ACS Catalysis, 2017, vol. 7, # 4, p. 3004 - 3009].
[13]Hong, Ji Li; Wang, Lei [European Journal of Organic Chemistry, 2006, # 22, p. 5099 - 5102].
[14]Location in patent: experimental part Wang, Lei; Li, Hongji; Li, Pinhua [Tetrahedron, 2009, vol. 65, # 1, p. 364 - 368].
[15]Location in patent: experimental part Gao, Shuiying; Huang, Yuanbiao; Cao, Minna; Liu, Tian-Fu; Cao, Rong [Journal of Materials Chemistry, 2011, vol. 21, # 41, p. 16467 - 16472].
[16]Nouri, Fatemeh; Rostamizadeh, Shahnaz; Azad, Mohammad [Inorganica Chimica Acta, 2018, vol. 471, p. 664 - 673].
[17]Buchmeiser, Michael R.; Wurst [Journal of the American Chemical Society, 1999, vol. 121, # 48, p. 11101 - 11107].
[18]Li, Hongji; Wang, Lei; Li, Pinhua [Synthesis, 2007, # 11, p. 1635 - 1642].
[19]Location in patent: experimental part Islam, Manirul; Mondal, Paramita; Roy, Anupam Singha; Tuhina, Kazi [Transition Metal Chemistry, 2010, vol. 35, # 4, p. 491 - 499].
[20]Li, Dan; Tian, Qingqiang; Wang, Xuetong; Wang, Qiang; Wang, Yin; Liao, Siwei; Xu, Ping; Huang, Xin; Yuan, Jianyong [Synthetic Communications, 2021, vol. 51, # 13, p. 2041 - 2052].
[21]Sarkar, Shaheen M.; Yusoff, Mashitah Mohd; Rahman, Md. Lutfor [Journal of the Chinese Chemical Society, 2015, vol. 62, # 1, p. 33 - 40].
[22]Wang, Furong; Tang, Sisi; Yu, Yinghao; Wang, Lefu; Yin, Biaolin; Li, Xuehui [Chinese Journal of Catalysis, 2014, vol. 35, # 12, p. 1921 - 1926].
[23]Mane, Pravin A.; Dey, Sandip; Vivekananda [Tetrahedron Letters, 2017, vol. 58, # 1, p. 25 - 29].
[24]Zhang, Sheng-Yan; Yu, Kai; Guo, Yu-Shuang; Mou, Rui-Qi; Lu, Xiao-Fan; Guo, Dian-Shun [ChemistryOpen, 2018, vol. 7, # 10, p. 803 - 813].
[25]Niakan, Mahsa; Masteri-Farahani, Majid; Shekaari, Hemayat; Karimi, Sabah [Carbohydrate Polymers, 2021, vol. 251].
[26]Location in patent: experimental part Hajipour, Abdol R.; Karami, Kazem; Tavakoli, Ghazal [Applied Organometallic Chemistry, 2010, vol. 24, # 11, p. 798 - 804].
[27]Location in patent: experimental part Hajipour, Abdol R.; Rafiee, Fatemeh [Journal of Organometallic Chemistry, 2011, vol. 696, # 13, p. 2669 - 2675].
[28]Location in patent: experimental part Hajipour, Abdol Reza; Rafiee, Fatemeh; Rouho, Arnold E. [Tetrahedron Letters, 2011, vol. 52, # 37, p. 4782 - 4787].
[29]Location in patent: experimental part Mondal, John; Modak, Arindam; Bhaumik, Asim [Journal of Molecular Catalysis A: Chemical, 2011, vol. 350, # 1-2, p. 40 - 48].
[30]Location in patent: experimental part Hajipour, Abdol R.; Rafiee, Fatemeh [Applied Organometallic Chemistry, 2011, vol. 25, # 7, p. 542 - 551].
[31]Sarkar, Shaheen M.; Rahman, Md. Lutfor; Yusoff, Mashitah Mohd [New Journal of Chemistry, 2015, vol. 39, # 5, p. 3564 - 3570].
[32]Mane, Pravin A.; Neogy, Suman; Dey, Sandip [Applied Organometallic Chemistry, 2020, vol. 34, # 3].
[33]Khalili, Dariush; Banazadeh, Ali Reza; Etemadi-Davan, Elham [Catalysis Letters, 2017, vol. 147, # 10, p. 2674 - 2687].
[34]Sadhasivam, Velu; Mathappan, Mariyappan; Harikrishnan, Muniyasamy; Chithiraikumar, Chinnadurai; Murugesan, Sepperumal; Siva, Ayyanar [Research on Chemical Intermediates, 2018, vol. 44, # 4, p. 2853 - 2866].
[35]Balinge, Kamlesh Rudreshwar; Bhagat, Pundlik Rambhau [Inorganica Chimica Acta, 2019, vol. 495].
[36]Mu, Bing; Li, Tiesheng; Xu, Wenjian; Zeng, Guoliang; Liu, Pingping; Wu, Yangjie [Tetrahedron, 2007, vol. 63, # 46, p. 11475 - 11488].
[37]Location in patent: experimental part Firouzabadi, Habib; Iranpoor, Nasser; Gholinejad, Mohammad [Tetrahedron, 2009, vol. 65, # 34, p. 7079 - 7084].
[38]Movassagh, Barahman; Rezaei, Nasrin [New Journal of Chemistry, 2015, vol. 39, # 10, p. 7988 - 7997].
[39]Fareghi-Alamdari, Reza; Haqiqi, Mohsen G.; Zekri, Negar [New Journal of Chemistry, 2016, vol. 40, # 2, p. 1287 - 1296].
[40]Naeimi, Hossein; Kiani, Fatemeh [Applied Organometallic Chemistry, 2019, vol. 33, # 3].
[41]Location in patent: experimental part Liu, Jie; Liu, Hongqiang; Wang, Lei [Applied Organometallic Chemistry, 2010, vol. 24, # 5, p. 386 - 391].
[42]Puthiaraj, Pillaiyar; Pitchumani, Kasi [Green Chemistry, 2014, vol. 16, # 9, p. 4223 - 4233].
[43]Jha, Abadh Kishor; Shahni, Rahul Kumar; Jain, Nidhi [Synlett, 2015, vol. 26, # 2, p. 259 - 264].
[44]Maji, Ankur; Singh, Ovender; Singh, Sain; Mohanty, Aurobinda; Maji, Pradip K.; Ghosh, Kaushik [European Journal of Inorganic Chemistry, 2020, vol. 2020, # 17, p. 1596 - 1611].
[45]Silberg, Josef; Schareina, Thomas; Kempe, Rhett; Wurst; Buchmeiser, Michael R. [Journal of Organometallic Chemistry, 2001, vol. 622, # 1-2, p. 6 - 18].
[46]Iranpoor, Nasser; Firouzabadi, Habib; Azadi, Roya [European Journal of Organic Chemistry, 2007, # 13, p. 2197 - 2201].
[47]Li, Hongfang; Lue, Jian; Lin, Jingxiang; Huang, Yuanbiao; Cao, Minna; Cao, Rong [Chemistry - A European Journal, 2013, vol. 19, # 46, p. 15661 - 15668].
[48]Movassagh, Barahman; Ranjbari, Shabnam [Applied Organometallic Chemistry, 2018, vol. 32, # 4].
[49]Cui, Xin; Li, Juan; Zhang, Zhi-Ping; Fu, Yao; Liu, Lei; Guo, Qing-Xiang [Journal of Organic Chemistry, 2007, vol. 72, # 24, p. 9342 - 9345].
[50]Sobhani, Sara; Falatooni, Zahra Mesbah; Asadi, Solmaz; Honarmand, Moones [Catalysis Letters, 2016, vol. 146, # 1, p. 255 - 268].
  • 6
  • [ 1552-41-6 ]
  • [ 100-52-7 ]
  • [ 13041-79-7 ]
YieldReaction ConditionsOperation in experiment
79% Stage #1: diethyl [(4-cyanophenyl)methyl]phosphonate With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 1h; Stage #2: benzaldehyde In tetrahydrofuran; mineral oil at 0 - 20℃; for 12h; 2.2. General synthesis procedure. General procedure: A solution of diethyl 4-cyanobenzyl-phosphonate (1.1 mmol) inanhydrous THF (20 ml) was cooled to 0 C, followed by addition ofNaH (55%) (1.2 mmol). After stirring for 1 h, substituted benzaldehyde(1.0 mmol) was added. Then, the reaction solution waswarmed to room temperature and stirred for another 12 h. Afterthe aldehyde was totally consumed, the reaction was quenchedby ice water (10 ml). The mixed solution was extracted twice withethyl acetate (10 ml). The organic layer was combined and washedwith saturated NaCl solution (20 ml). After dried over Na2SO4, theorganic solvents were evaporated under vacuum. The crude productwas then recrystallized in ethyl acetate or purified througha silica gel column using petroleum ether and ethyl acetate as elutesolvent (PE:EA = 12:1). Finally, trans-isomer of substituted 4-styrylbenzonitrile was obtained as white solid. 2.2.1. 4-(2-Phenylethenyl)benzonitrile (1)Yield: 79%. M.p: 112-115 C. 1H NMR (500 MHz, CDCl3) d 7.68(d, J = 8.3 Hz, 2H), 7.63 (d, J = 8.1 Hz, 2H), 7.58 (d, J = 7.6 Hz,2H), 7.44 (t, J = 7.5 Hz, 2H), 7.36 (t, J = 7.3 Hz, 1H), 7.26 (d,J = 16.3 Hz, 1H), 7.14 (d, J = 16.3 Hz, 1H). 13C NMR (126 MHz, CDCl3)d 141.3, 135.8, 132.0, 131.9, 128.4, 128.2, 126.4, 126.4, 126.2,118.6, 110.1. HRMS (ESI) calcd. for C15H12N [M+H]+: 206.0964,found: 206.0965.
Stage #1: diethyl [(4-cyanophenyl)methyl]phosphonate With sodium methylate In N,N-dimethyl-formamide at 0℃; Stage #2: benzaldehyde In N,N-dimethyl-formamide at 20℃; Further stages.;
  • 7
  • [ 9003-53-6 ]
  • [ 32792-60-2 ]
  • [ 13041-79-7 ]
  • [ 81329-28-4 ]
YieldReaction ConditionsOperation in experiment
83% With isoquinoline; lithium chloride In various solvent(s) at 160℃;
  • 8
  • [ 623-00-7 ]
  • [ CAS Unavailable ]
  • [ 13041-79-7 ]
YieldReaction ConditionsOperation in experiment
84% With 2C8H8NO2(1-)*2Cl(1-)*2Pd(2+); tetrabutylammomium bromide; potassium carbonate In water at 120℃; for 14h; Sealed vessel; stereoselective reaction;
80% With <i>tert</i>-butylamine In water; isopropyl alcohol for 6h; Heating;
  • 9
  • [ 100-52-7 ]
  • [ 2067400-50-2 ]
  • [ 13041-79-7 ]
  • [ 14064-68-7 ]
YieldReaction ConditionsOperation in experiment
1: 66% 2: 13% Stage #1: (E)-N'-(4-cyanobenzylidene)-4-methylbenzenesulfonohydrazide With potassium <i>tert</i>-butylate In toluene at 0 - 20℃; for 1h; Stage #2: benzaldehyde With 5,10,15,20-tetraphenyl porphyrinato iron hydroxide; Aliquat 336; phosphorous acid trimethyl ester In toluene at 40℃; for 48h;
  • 10
  • [ 9003-53-6 ]
  • [ 623-00-7 ]
  • [ 13041-79-7 ]
  • [ 81329-28-4 ]
YieldReaction ConditionsOperation in experiment
With sodium acetate In N,N-dimethyl-formamide at 130℃; for 24h; Title compound not separated from byproducts;
With tetrabutyl-ammonium chloride; sodium carbonate In 1-methyl-pyrrolidin-2-one at 150℃; for 6h; Title compound not separated from byproducts;
  • 11
  • [ 9003-53-6 ]
  • [ 6068-72-0 ]
  • [ 13041-79-7 ]
YieldReaction ConditionsOperation in experiment
73% With [{RhCl(C2H4)2}2] In o-xylene for 6h; Heating;
73% In xylene for 6h; Heating;
  • 12
  • [ 1080-32-6 ]
  • [ 105-07-7 ]
  • [ 13041-79-7 ]
YieldReaction ConditionsOperation in experiment
Stage #1: O,O-diethyl benzylphosphonate With 18-crown-6 ether; sodium methylate In N,N-dimethyl-formamide at 20℃; for 0.0833333h; Stage #2: 4-cyanobenzaldehyde In N,N-dimethyl-formamide at 20 - 120℃; for 6h;
  • 13
  • [ 123-75-1 ]
  • [ 623-00-7 ]
  • [ 536-74-3 ]
  • [ 10282-30-1 ]
  • [ 13041-79-7 ]
  • [ 29822-79-5 ]
  • [ 14064-68-7 ]
YieldReaction ConditionsOperation in experiment
1: 70% 2: 14% 3: 6% 4: 10% With triphenylphosphine; 1-butyl-3-methylimidazolium Tetrafluoroborate at 130℃; for 20h;
  • 14
  • [ 105-07-7 ]
  • [ 13041-79-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: 83 percent / methanol / 0.5 h / 20 °C 2.1: t-BuOK / toluene / 1 h / 0 - 20 °C 2.2: 66 percent / Aliquat(R) 336; meso-tetraphenylporphyrin iron chloride; P(OMe)3 / toluene / 48 h / 40 °C
 

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