C-H Amination via Electrophotocatalytic Ritter-type Reaction

J Am Chem Soc. 2021 Jun 16;143(23):8597-8602. doi: 10.1021/jacs.1c03718. Epub 2021 Jun 2.

Abstract

A method for C-H bond amination via an electrophotocatalytic Ritter-type reaction is described. The reaction is catalyzed by a trisaminocyclopropenium (TAC) ion in an electrochemical cell under irradiation. These conditions convert benzylic C-H bonds to acetamides without the use of a stoichiometric chemical oxidant. A range of functionality is shown to be compatible with this transformation, and several complex substrates are demonstrated.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Acetamides / chemical synthesis*
  • Acetamides / chemistry
  • Amination
  • Catalysis
  • Cyclopropanes / chemistry*
  • Molecular Structure

Substances

  • Acetamides
  • Cyclopropanes