Electrochemical Sulfonylation/Heteroarylation of Alkenes via Distal Heteroaryl ipso-Migration

Ming Wei Zheng; Xin Yuan; Yu Sheng Cui; Jiang Kai Qiu; Guigen Li; Kai Guo

doi:10.1021/acs.orglett.8b03191

Electrochemical Sulfonylation/Heteroarylation of Alkenes via Distal Heteroaryl ipso-Migration

Ming Wei Zheng, Xin Yuan, Yu Sheng Cui, Jiang Kai Qiu, Guigen Li, Kai Guo

COLLEGE OF BIOTECHNOLOGY AND PHARMACEUTICAL ENGINEERING

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

71 Scopus citations

Abstract

A direct electrooxidative sulfonylation/heteroarylation reaction of alkenes with sulfinic acids, which proceeds through distal heteroaryl ipso-migration and C-S and C-C bond formations, is reported. This electro-synthetic method offers an efficient and environmentally friendly entry to prepare various sulfonated functionalized heteroarenes under an undivided cell at room temperature, avoiding the use of any metal catalysts, additives, and oxidants. Preliminary mechanistic studies indicated a radical pathway.

Original language	English
Pages (from-to)	7784-7789
Number of pages	6
Journal	Organic Letters
Volume	20
Issue number	24
DOIs	https://doi.org/10.1021/acs.orglett.8b03191
State	Published - 21 Dec 2018

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title = "Electrochemical Sulfonylation/Heteroarylation of Alkenes via Distal Heteroaryl ipso-Migration",

abstract = "A direct electrooxidative sulfonylation/heteroarylation reaction of alkenes with sulfinic acids, which proceeds through distal heteroaryl ipso-migration and C-S and C-C bond formations, is reported. This electro-synthetic method offers an efficient and environmentally friendly entry to prepare various sulfonated functionalized heteroarenes under an undivided cell at room temperature, avoiding the use of any metal catalysts, additives, and oxidants. Preliminary mechanistic studies indicated a radical pathway.",

author = "Zheng, {Ming Wei} and Xin Yuan and Cui, {Yu Sheng} and Qiu, {Jiang Kai} and Guigen Li and Kai Guo",

note = "Publisher Copyright: {\textcopyright} 2018 American Chemical Society.",

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doi = "10.1021/acs.orglett.8b03191",

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T1 - Electrochemical Sulfonylation/Heteroarylation of Alkenes via Distal Heteroaryl ipso-Migration

AU - Zheng, Ming Wei

AU - Yuan, Xin

AU - Cui, Yu Sheng

AU - Qiu, Jiang Kai

AU - Li, Guigen

AU - Guo, Kai

PY - 2018/12/21

Y1 - 2018/12/21

N2 - A direct electrooxidative sulfonylation/heteroarylation reaction of alkenes with sulfinic acids, which proceeds through distal heteroaryl ipso-migration and C-S and C-C bond formations, is reported. This electro-synthetic method offers an efficient and environmentally friendly entry to prepare various sulfonated functionalized heteroarenes under an undivided cell at room temperature, avoiding the use of any metal catalysts, additives, and oxidants. Preliminary mechanistic studies indicated a radical pathway.

AB - A direct electrooxidative sulfonylation/heteroarylation reaction of alkenes with sulfinic acids, which proceeds through distal heteroaryl ipso-migration and C-S and C-C bond formations, is reported. This electro-synthetic method offers an efficient and environmentally friendly entry to prepare various sulfonated functionalized heteroarenes under an undivided cell at room temperature, avoiding the use of any metal catalysts, additives, and oxidants. Preliminary mechanistic studies indicated a radical pathway.

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U2 - 10.1021/acs.orglett.8b03191

DO - 10.1021/acs.orglett.8b03191

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AN - SCOPUS:85059664086

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JO - Organic Letters

JF - Organic Letters

IS - 24

ER -

Electrochemical Sulfonylation/Heteroarylation of Alkenes via Distal Heteroaryl ipso-Migration

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