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Generation of β‐Halo Vinylsulfones through a Multicomponent Reaction with Insertion of Sulfur Dioxide
Author(s) -
Xiang Yuanchao,
Kuang Yunyan,
Wu Jie
Publication year - 2017
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.201701465
Subject(s) - chemistry , halogenation , sulfur dioxide , halide , dabco , stereoselectivity , sulfur , halo , inorganic chemistry , medicinal chemistry , organic chemistry , catalysis , physics , quantum mechanics , galaxy
A four‐component reaction of terminal alkynes, aryldiazonium tetrafluoroborates, sulfur dioxide surrogate of DABCO⋅(SO 2 ) 2 , and potassium halide in the presence of copper(I) chloride (10 mol %) gives rise to β‐halo vinylsulfones with good stereoselectivity. The vicinal difunctionalization of alkynes through sulfonylation and halogenation with the insertion of sulfur dioxide works efficiently. A plausible mechanism is proposed, which includes a radical process.
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