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Electrochemically Initiated Formation of Sulfonyl Radicals: Synthesis of Oxindoles Via Difunctionalization of Acrylamides Mediated By Bromide Ion

Monday, 29 May 2017: 09:05
Grand Salon C - Section 16 (Hilton New Orleans Riverside)
C. Zeng (Beijing University of Technology, College of Life Science & Bioengineering) and Y. Jiang (Beijing University of Technology)
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 catalytic amount of NH4Br (10 mmol %) as a redox catalyst. The protocol is practical that is proved by the one-pot, two-step procedure and scaled-up experiments. Mechanical studies reveal that the electrochemical approach involves the formation of sulfonyl radicals via homolytic cleavage of the in-situ generated sulfonyl bromide.

Scheme 1. Oxidative radical coupling for the synthesis of oxindoles