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Oxidant-directed chemoselective sulfonylation and sulfonyloximation of alkenes via cleaving the C–S bond in TosMIC

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Abstract

Oxidant-directed chemoselective sulfonylation and sulfonyloximation reactions for the divergent synthesis of valuable vinyl sulfones and α-sulfonylethanone oximes starting from simple alkenes and TosMIC by using tert-butyl hydroperoxide and tert-butyl nitrite, respectively, as terminal oxidants were developed. The success of this method could be attributed to the combination of a cobalt catalyst and a perfluoroalkyl halide additive. The feasibility of performing the reactions on a large scale potentially allows the further application of the method in industrial manufacture.

Graphical abstract: Oxidant-directed chemoselective sulfonylation and sulfonyloximation of alkenes via cleaving the C–S bond in TosMIC

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Publication details

The article was received on 12 Dec 2018, accepted on 03 Feb 2019 and first published on 04 Feb 2019


Article type: Research Article
DOI: 10.1039/C8QO01346B
Citation: Org. Chem. Front., 2019, Advance Article

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    Oxidant-directed chemoselective sulfonylation and sulfonyloximation of alkenes via cleaving the C–S bond in TosMIC

    X. Chu, D. Ge, T. Loh and Z. Shen, Org. Chem. Front., 2019, Advance Article , DOI: 10.1039/C8QO01346B

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