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

Abstract

A metal-free gem-functionalization reaction of diazo compounds with N-sulfenylsuccinimides via a formal N–S bond insert process has been reported. The transformation features mild reaction conditions, broad substrate scope and functional group tolerance, offering an efficient approach to sulfides 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.

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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., 2017, Accepted Manuscript
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    Thermally induced N-S bond insertion reaction of diazo compounds with N-sulfenylsuccinimides: synthresis of sulfides and mechanism studies

    X. Xu, X. Zhang, Y. Zheng and L. Qiu, Org. Biomol. Chem., 2017, Accepted Manuscript , DOI: 10.1039/C7OB02488F

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