Visible light-mediated radical-cascade addition/cyclization of arylacrylamides with aldehydes to form quaternary oxindoles at room temperature. Issue 13 (23rd May 2022)

• Record Type: Journal Article
• Authors: Sun, Zhaozhao; Huang, Huawen; Wang, Qiaolin; Huang, Chunyan; Mao, Guojiang; Deng, Guo-Jun
• Is Part Of: Organic chemistry frontiers. Volume 9:Issue 13(2022)
• Page Start: 3506
• Page End: 3514
• Publication Date: 2022-05-23
• Subjects: Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1039/d2qo00319h
• Languages: English
• ISSNs: 2052-4110

Abstract

Abstract : The visible light-induced oxidative radical cascade coupling of N -arylacrylamides with aldehydes using bromide as the hydrogen atom transfer agent to synthesize functional oxindoles is described. Abstract : A visible-light-mediated oxidative cyclization of N -arylacrylamides by a radical cascade with readily available aliphatic or aromatic aldehydes was achieved. This transformation provides an operationally convenient, mild, and efficient access to various alkyl-substituted or acyl-substituted oxindoles at room temperature under metal-free conditions. This protocol features good functional group tolerance and high chemoselectivity with general yields ranging from moderate to good. Mechanistic studies reveal that the bromo radical probably plays a promotional role in the formation of the acyl radical via HAT.