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Electrochemical Alkynyl/Alkenyl Migration for the Radical Difunctionalization of Alkenes
Author(s) -
Gao Yongyuan,
Mei Haibo,
Han Jianlin,
Pan Yi
Publication year - 2018
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201804157
Subject(s) - sulfonyl , chemistry , electrochemistry , alkynylation , catalysis , combinatorial chemistry , organic chemistry , alkyl , electrode
An efficient electrochemical 1,2‐sulfonylation/alkynylation of alkenes via radical 1,4‐alkynyl migration of alkynyl‐substituted tertiary alcohols is described, which used sodium sulfinates as sulfonyl sources affording the corresponding α‐sulfonyl‐β‐alkynylated products in moderate to excellent yields. This electrochemical reaction proceeds smoothly without the use of any metal catalyst, additive and oxidant and thus represents a new and eco‐friendly strategy for the difunctionalization of unactive olefins, and also the first example of the electrochemical distal radical migration reaction.