4.8 Article

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

Journal

ORGANIC LETTERS
Volume 20, Issue 24, Pages 7784-7789

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.8b03191

Keywords

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Funding

  1. National Natural Science Foundation of China [21702103, 21522604, U1463201, 21402240]
  2. Youth in Jiangsu Province Natural Science Fund [BK20150031, BK20130913, BY2014005-03]

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A direct electrooxidative sulfonylation/hetero-arylation 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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