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

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.

Automated summary

An electrochemical carbenoid insertion reaction using diazo compounds as reagents and electricity as the oxidant has been developed. This transformation proceeds smoothly under mild conditions at room temperature without the need for a catalyst or ligand. The yield of the S-H insertion product reaches up to 96% and the O-H product can be efficiently obtained with a yield of up to 80%. Importantly, this environmentally friendly strategy demonstrates excellent applicability in gram-scale synthesis.