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MnO 2 ‐Promoted Oxidative Radical Sulfonylation of Haloalkynes with Sulfonyl Hydrazides: C(sp)–S Bond Formation towards Alkynyl Sulfones
Author(s) -
Chen Pengquan,
Zhu Chuanle,
Zhu Rui,
Wu Wanqing,
Jiang Huanfeng
Publication year - 2017
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201700550
Subject(s) - sulfonyl , chemistry , oxidative phosphorylation , medicinal chemistry , catalysis , oxidative coupling of methane , polymer chemistry , organic chemistry , biochemistry , alkyl
A catalyst‐free oxidative radical sulfonylation of haloalkynes with sulfonyl hydrazides is reported. It represents an example of C(sp)−S bond formation using sulfonyl hydrazides as sulfonyl radical sources. Various alkynyl sulfones were synthesized in moderate to good yields. Having MnO 2 as the oxidant is very critical for this transformation. Remarkably, the self‐coupling reaction of haloalkynes through C(sp)−C(sp) bond formation is significantly inhibited under the standard reaction conditions.