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Thermally induced N–S bond insertion reaction of diazo compounds with N-sulfenylsuccinimides: synthesis of sulfides and mechanism studies

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Abstract

A metal-free gem-functionalization reaction of diazo compounds with N-sulfenylsuccinimides via a formal N–S bond insertion process has been reported. The transformation features mild reaction conditions, broad substrate scope and functional group tolerance, offering an efficient approach to sulfide synthesis in moderate to high yields. In addition, the mechanism studies indicate the formation of free carbene under thermal conditions followed by ylide generation, then N–S bond cleavage and C–N bond formation occurred in sequence to give the sulfide products.

Graphical abstract: Thermally induced N–S bond insertion reaction of diazo compounds with N-sulfenylsuccinimides: synthesis of sulfides and mechanism studies

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Publication details

The article was received on 08 Oct 2017, accepted on 13 Nov 2017 and first published on 13 Nov 2017


Article type: Paper
DOI: 10.1039/C7OB02488F
Citation: Org. Biomol. Chem., 2018, Advance Article
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    Thermally induced N–S bond insertion reaction of diazo compounds with N-sulfenylsuccinimides: synthesis of sulfides and mechanism studies

    X. Zhang, Y. Zheng, L. Qiu and X. Xu, Org. Biomol. Chem., 2018, Advance Article , DOI: 10.1039/C7OB02488F

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