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

Org Biomol Chem. 2022 Oct 26;20(41):8078-8082. doi: 10.1039/d2ob01273a.

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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Esters* / chemistry
  • Ligands
  • Oxidants
  • Salicylates
  • Sulfhydryl Compounds*

Substances

  • Esters
  • Sulfhydryl Compounds
  • Salicylates
  • Ligands
  • Oxidants