Heteroatom-Assisted Regio- and Stereoselective Palladium-Catalyzed Carboxylation of 9-Allyl Adenine

J Org Chem. 2022 Oct 7;87(19):12574-12585. doi: 10.1021/acs.joc.2c00659. Epub 2022 Sep 29.

Abstract

Strategy for the synthesis of acyclic nucleoside analogs of biological relevance via highly regio- and stereoselective C-H functionalization employing heteroatom-assisted palladium-catalyzed carboxylation of 9-allyl adenine is disclosed. Substrate scope with different carboxylic acids was performed giving decent to good yields of the desired products. The method also allowed for the synthesis of deuterated analogs.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Adenine*
  • Carboxylic Acids
  • Catalysis
  • Nucleosides
  • Palladium*

Substances

  • Carboxylic Acids
  • Nucleosides
  • Palladium
  • Adenine