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.