Rhodium-Catalyzed Deuterated Tsuji-Wilkinson Decarbonylation of Aldehydes with Deuterium Oxide

J Am Chem Soc. 2022 Jun 29;144(25):11081-11087. doi: 10.1021/jacs.2c04422. Epub 2022 Jun 16.

Abstract

The recent surge in the applications of deuterated drug candidates has rendered an urgent need for diverse deuterium labeling techniques. Herein, an efficient Rh-catalyzed deuterated Tsuji-Wilkinson decarbonylation of naturally available aldehydes with D2O is developed. In this reaction, D2O not only acts as a deuterated reagent and solvent but also promotes Rh-catalyzed decarbonylation. In addition, decarbonylative strategies for the synthesis of terminal monodeuterated alkenes from α,β-unsaturated aldehydes are within reach.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aldehydes
  • Alkenes
  • Catalysis
  • Deuterium Oxide
  • Rhodium*

Substances

  • Aldehydes
  • Alkenes
  • Rhodium
  • Deuterium Oxide