Regioselective synthesis of benzonitriles via amino-catalyzed [3+3] benzannulation reaction. Issue 9 (September 2020)

• Record Type: Journal Article
• Authors: Jiang, Lin; Jin, Wen-Fei; Yu, Liu-Dong; Yuan, Ming-Wei; Li, Hong-Li; Jiang, Deng-Bang; Yuan, Ming-Long
• Is Part Of: Journal of chemical research. Volume 44:Issue 9/10(2020)
• Page Start: 592
• Page End: 597
• Publication Date: 2020-09
• Subjects: α, β-unsaturated aldehyde -- 4-arylsulfonyl-2-butenenitrile -- aminocatalysis -- benzannulation -- benzonitrile; Chemistry -- Research -- Periodicals; Chemistry -- Periodicals; 540.5
• DOI: 10.1177/1747519820915163
• Languages: English
• ISSNs: 1747-5198

Abstract

A straightforward synthesis of benzonitriles is achieved via amino-catalyzed [3+3] benzannulation of α, β-unsaturated aldehydes and 4-arylsulfonyl-2-butenenitriles. Using pyrrolidine as an organocatalyst via iminium activation, a series of substituted benzonitriles were obtained in good to high yields in a regioselective manner. This reaction can proceed smoothly under mild reaction conditions and without the aid of any metals, additional oxidants, or strong bases, thus making this an efficient and environmentally friendly method to access benzonitriles.