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

Xue Qiang Chu; Danhua Ge; Teck Peng Loh; Zhi Liang Shen

doi:10.1039/c8qo01346b

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

Xue Qiang Chu, Danhua Ge, Teck Peng Loh^*, Zhi Liang Shen

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

36 Citations (Scopus)

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.

Original language	English
Pages (from-to)	835-840
Number of pages	6
Journal	Organic Chemistry Frontiers
Volume	6
Issue number	6
DOIs	https://doi.org/10.1039/c8qo01346b
Publication status	Published - Mar 21 2019
Externally published	Yes

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© 2019 the Partner Organisations.

ASJC Scopus Subject Areas

Organic Chemistry

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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.",

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AU - Loh, Teck Peng

AU - Shen, Zhi Liang

PY - 2019/3/21

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AB - 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.

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

Abstract

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