Pd-Catalyzed regio- and stereoselective allylic substitution of vinylethylene carbonates with 1,2,4-triazoles

Org Biomol Chem. 2022 Aug 24;20(33):6532-6536. doi: 10.1039/d2ob01156e.

Abstract

N 1-Substituted 1,2,4-triazoles are ubiquitous skeletons in medicinal agents, agrochemicals, and organic materials. Herein, an efficient and practical method for the synthesis of N1-allylated 1,2,4-triazoles via Pd-catalyzed allylic substitution of vinylethylene carbonates (VECs) with 1,2,4-triazoles has been developed. By using a catalyst generated in situ from Pd2(dba)3·CHCl3 and DPPE under mild conditions, the process allows rapid access to N1-allylated 1,2,4-triazoles bearing diverse functionalities in high yields with excellent N1-selectivities, linear-selectivities, and Z-stereoselectivities.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Carbonates
  • Catalysis
  • Palladium*
  • Stereoisomerism
  • Triazoles*

Substances

  • Carbonates
  • Triazoles
  • Palladium