3 years ago

MnO2-Promoted Oxidative Radical Sulfonylation of Haloalkynes with Sulfonyl Hydrazides: C(sp)–S Bond Formation towards Alkynyl Sulfones

MnO2-Promoted Oxidative Radical Sulfonylation of Haloalkynes with Sulfonyl Hydrazides: C(sp)–S Bond Formation towards Alkynyl Sulfones
Huanfeng Jiang, Wanqing Wu, Rui Zhu, Pengquan Chen, Chuanle Zhu
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 MnO2 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. C(sp)−S Bond Formation: A catalyst-free oxidative radical sulfonylation of haloalkynes with sulfonyl hydrazides has been developed. Various alkynyl sulfones were synthesized in moderate to good yields, and MnO2 was used as the oxidant.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/asia.201700550

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