Issue 41, 2022

Electrochemical S–H and O–H insertion reactions from thiols or salicylic acids with diazo esters

Abstract

An electrochemical carbenoid insertion reaction of diazo compounds into C–S and C–O bonds with electricity as the oxidant has been reported in this work. In this protocol, this transformation proceeded smoothly under mild conditions at room temperature in the absence of a catalyst and a ligand. In addition, the yield of the S–H insertion product was up to 96% and the O–H product could be efficiently obtained in up to 80% yield. Of note is that this environmentally friendly strategy exhibited excellent applicability in gram-scale synthesis.

Graphical abstract: Electrochemical S–H and O–H insertion reactions from thiols or salicylic acids with diazo esters

Supplementary files

Article information

Article type
Paper
Submitted
16 Jul 2022
Accepted
28 Sep 2022
First published
29 Sep 2022

Org. Biomol. Chem., 2022,20, 8078-8082

Electrochemical S–H and O–H insertion reactions from thiols or salicylic acids with diazo esters

Z. He, W. Zhao, Y. Li, Y. Yu and F. Huang, Org. Biomol. Chem., 2022, 20, 8078 DOI: 10.1039/D2OB01273A

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