Thermally induced N–S bond insertion reaction of diazo compounds with N-sulfenylsuccinimides: synthesis of sulfides and mechanism studies
Literature Information
Xiaolu Zhang, Yang Zheng, Lihua Qiu
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.
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Organic & Biomolecular Chemistry

Organic & Biomolecular Chemistry (OBC) publishes original and high impact research and reviews in organic chemistry. We welcome research that shows new or significantly improved protocols or methodologies in total synthesis, synthetic methodology or physical and theoretical organic chemistry as well as research that shows a significant advance in the organic chemistry or molecular design aspects of chemical biology, catalysis, supramolecular and macromolecular chemistry, theoretical chemistry, mechanism-oriented physical organic chemistry, medicinal chemistry or natural products. Articles published in the journal should report new work which makes a highly-significant impact in the field. Routine and incremental work is generally not suitable for publication in the journal. More details about key areas of our scope are below. In all cases authors should include in their article clear rationale for why their research has been carried out.




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