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Synthesis of γ-substituted carbonyl compounds from DMSO-mediated oxidation of enynamides: mechanistic insights and carbon- and hetero-functionalizations

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Abstract

Oxidative coupling of 1,3-enynamides using DMSO as a terminal oxidant has been developed. Carbon as well as unmodified heteroatom nucleophiles, including aliphatic alcohols, thiols, and hydrazides, could be efficiently alkylated at the γ-position in a highly regioselective fashion. The kinetic analysis suggested a nucleophile-dependent mechanism ranging from a concerted SN2′′ to a carbocationic mechanism. Thus, the remote site-selectivity was ascribed to the partial positive charge developing at the terminal carbocationic center.

Graphical abstract: Synthesis of γ-substituted carbonyl compounds from DMSO-mediated oxidation of enynamides: mechanistic insights and carbon- and hetero-functionalizations

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Publication details

The article was received on 24 Jul 2019, accepted on 04 Aug 2019 and first published on 12 Aug 2019


Article type: Edge Article
DOI: 10.1039/C9SC03663F
Chem. Sci., 2019, Advance Article
  • Open access: Creative Commons BY-NC license
    All publication charges for this article have been paid for by the Royal Society of Chemistry

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    Synthesis of γ-substituted carbonyl compounds from DMSO-mediated oxidation of enynamides: mechanistic insights and carbon- and hetero-functionalizations

    Q. H. Nguyen, N. H. Nguyen, H. Kim and S. Shin, Chem. Sci., 2019, Advance Article , DOI: 10.1039/C9SC03663F

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