Unexpected Decarboxamidation of α-Arylsulfonyl Weinreb Amides by Grignard Reagents: Synthesis of α-Disubstituted Arylsulfones

doi:10.1007/s40242-017-6371-z

Abstract

Abstract:

An unexpected decarboxamidation of α-arylsulfonyl Weinreb amides as a side reaction under the standard acylating conditions was found in Weinreb amides chemistry. The control experiments for mechanism study disclosed that α-sulfo group was necessary, and α-quaternary carbon was the key factor for the reaction. Meanwhile, an efficient method was established for the preparation of secondary alkyl arylsulfones by this unexpected C-C bond cleavage reaction using excess Grignard reagent.

Key words: Weinreb amide, Sulfone, Grignard reagent, C-C bond cleavage, Decarboxamidation

LIU Wei, LI Houying, QIN Haijuan, ZHAO Wei, ZHOU Chen, JIANG Shengping, YANG Cheng. Unexpected Decarboxamidation of α-Arylsulfonyl Weinreb Amides by Grignard Reagents: Synthesis of α-Disubstituted Arylsulfones[J]. Chemical Research in Chinese Universities, 2017, 33(2): 213-220.

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