A novel and convenient synthesis of benzonitriles: electrophilic cyanation of aryl and heteroaryl bromides

P Anbarasan, H Neumann…

Index: Anbarasan, Pazhamalai; Neumann, Helfried; Beller, Matthias Chemistry - A European Journal, 2011 , vol. 17, # 15 p. 4217 - 4222

Full Text: HTML

Citation Number: 65

Abstract

Abstract N-Cyano-N-phenyl-p-methylbenzenesulfonamide has been used as a more benign electrophilic cyanation reagent for the synthesis of various benzonitriles from (hetero) aryl bromides via formation of Grignard reagents. Electronically different and sterically demanding aryl bromides including functionalized substrates and heteroaryl bromides are successfully cyanated in good to excellent yields. The efficiency of the present ...

~47%

~78%

~95%

~76%

~63%

~77%

~86%

~72%

~83%

~70%

~68%

~69%

~73%

~71%

~80%

~78%

~82%

~83%

~78%

~88%

Phosphonium salt-catalysed synthesis of nitriles from in sit...

[Denton, Ross M.; An, Jie; Lindovska, Petra; Lewis, William Tetrahedron, 2012 , vol. 68, # 13 p. 2899 - 2905]

Reactions of trimethylsilyl azide with aldehydes: facile and...

[Nishiyama, Kozaburo; Oba, Makoto; Watanabe, Akio Tetrahedron, 1987 , vol. 43, # 4 p. 693 - 700]

Oxidative fragmentation of oxiranes to nitriles with hyperva...

[Deshmukh, Swapnil S.; Huddar, Sameerana N.; Jadhav, Ravindra R.; Akamanchi, Krishnacharya G. Tetrahedron Letters, 2011 , vol. 52, # 35 p. 4533 - 4536]

Facile transformation of esters to nitriles

[Suzuki, Yusuke; Moriyama, Katsuhiko; Togo, Hideo Tetrahedron, 2011 , vol. 67, # 41 p. 7956 - 7962]

Practical one-pot conversion of aryl bromides and β-bromosty...

[Ishii, Genki; Harigae, Ryo; Moriyama, Katsuhiko; Togo, Hideo Tetrahedron, 2013 , vol. 69, # 5 p. 1462 - 1469]