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

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.