Electrochemical borylation of carboxylic acids

Proc Natl Acad Sci U S A. 2021 Aug 24;118(34):e2109408118. doi: 10.1073/pnas.2109408118.

Abstract

A simple electrochemically mediated method for the conversion of alkyl carboxylic acids to their borylated congeners is presented. This protocol features an undivided cell setup with inexpensive carbon-based electrodes and exhibits a broad substrate scope and scalability in both flow and batch reactors. The use of this method in challenging contexts is exemplified with a modular formal synthesis of jawsamycin, a natural product harboring five cyclopropane rings.

Keywords: electrochemistry; organic synthesis; total synthesis.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Boronic Acids / chemistry*
  • Carboxylic Acids / chemistry*
  • Electrochemical Techniques / methods*
  • Electrodes*

Substances

  • Boronic Acids
  • Carboxylic Acids