Electrochemically initiated formation of sulfonyl radicals: synthesis of oxindoles via difunctionalization of acrylamides mediated by bromide ion. Issue 23 (20th September 2016)

• Record Type: Journal Article
• Authors: Jiang, Yang-Ye; Liang, Sen; Zeng, Cheng-Chu; Hu, Li-Ming; Sun, Bao-Guo
• Is Part Of: Green chemistry. Volume 18:Issue 23(2016)
• Page Start: 6311
• Page End: 6319
• Publication Date: 2016-09-20
• Subjects: Environmental chemistry -- Industrial applications -- Periodicals; Environmental management -- Periodicals; 660
• DOI: 10.1039/c6gc01970f
• Languages: English
• ISSNs: 1463-9262

Abstract

Abstract : Electrochemical access to oxindoles has been developed using NH4 Br as a mediator in an undivided cell. Abstract : An efficient electrochemical approach for the synthesis of oxindoles has been developed from electrolysis of a mixture of sodium sulfinate and acrylamide. The chemistry avoids the utilization of additional conducting salt and proceeds in a simple undivided cell employing a catalytic amount of NH4 Br (10 mmol%) as a redox catalyst. The protocol is practical, as proved by the one-pot, two-step procedure and scaled-up experiments. Mechanistic studies reveal that the electrochemical approach involves the formation of sulfonyl radicals via homolytic cleavage of in situ generated sulfonyl bromide.