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Redox-active benzimidazolium sulfonamides as cationic thiolating reagents for reductive cross-coupling of organic halides.

ABSTRACT: Redox-active benzimidazolium sulfonamides as thiolating reagents have been developed for reductive C-S bond coupling. The IMDN-SO₂R reagent provides a bench-stable cationic precursor to generate a portfolio of highly active N-S intermediates, which can be successfully applied in cross-electrophilic coupling with various organic halides. The employment of an electrophilic sulfur source solved the problem of catalyst deactivation and avoided odorous thiols, featuring practical conditions, broad substrate scope, and excellent tolerance.

SUBMITTER: Zhang W

PROVIDER: S-EPMC8179258 | biostudies-literature | 2020 Dec

REPOSITORIES: biostudies-literature

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Redox-active benzimidazolium sulfonamides as cationic thiolating reagents for reductive cross-coupling of organic halides.

Zhang Weigang W Huang Mengjun M Zou Zhenlei Z Wu Zhengguang Z Ni Shengyang S Kong Lingyu L Zheng Youxuan Y Wang Yi Y Pan Yi Y

Chemical science 20201222 7

Redox-active benzimidazolium sulfonamides as thiolating reagents have been developed for reductive C-S bond coupling. The IMDN-SO<sub>2</sub>R reagent provides a bench-stable cationic precursor to generate a portfolio of highly active N-S intermediates, which can be successfully applied in cross-electrophilic coupling with various organic halides. The employment of an electrophilic sulfur source solved the problem of catalyst deactivation and avoided odorous thiols, featuring practical condition ...[more]

PMID: 34164018

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