Palladium-Catalyzed Decarbonylative Cyanation of Carboxylic Acids with TMSCN

J Org Chem. 2022 Sep 2;87(17):11871-11879. doi: 10.1021/acs.joc.2c01375. Epub 2022 Aug 11.

Abstract

The direct decarbonylative cyanation of benzoic acids with TMSCN was achieved through palladium catalysis. By this strategy, a wide range of nitriles including those with functional groups was synthesized in good to high yields. Moreover, this reaction applied to modifying bioactive molecules such as adapalene, probenecid, telmisartan, and 3-methylflavone-8-carboxylic acid. These results demonstrate that this new reaction has potential synthetic value in organic synthesis.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Carboxylic Acids*
  • Catalysis
  • Cyanides
  • Palladium*
  • Trimethylsilyl Compounds

Substances

  • Carboxylic Acids
  • Cyanides
  • Trimethylsilyl Compounds
  • Palladium
  • trimethylsilyl cyanide