Electrochemical Amidation: Benzoyl Hydrazine/Carbazate and Amine as Coupling Partners

Org Lett. 2022 Sep 16;24(36):6619-6624. doi: 10.1021/acs.orglett.2c02626. Epub 2022 Sep 7.

Abstract

An electrochemical amidation of benzoyl hydrazine/carbazate and primary/secondary amine as coupling partners via concomitant cleavage and formation of C(sp2)-N bonds has been achieved. This methodology proceeds under metal-free and exogenous oxidant-free conditions producing N2 and H2 as byproducts. Mechanistic studies reveal the in situ generations of both acyl and N-centered radicals from benzoyl hydrazines and amines. The utility of this protocol is demonstrated through a large-scale, and synthesis of bezafibrate, a hyperlipidemic drug.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amines* / chemistry
  • Bezafibrate*
  • Hydrazines / chemistry

Substances

  • Amines
  • Hydrazines
  • hydrazine
  • carbazic acid
  • Bezafibrate