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

Organic Chemistry Frontiers Pub Date: 2019-02-04 DOI: 10.1039/C8QO01346B

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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