N -Allylbenzimidazole as a strategic surrogate in Rh-catalyzed stereoselective trans -propenylation of aryl C(sp 2 )-H bond.

Pragati BiswalTanmayee NandaShyam Kumar BanjareSmruti Ranjan MohantyRanjit Mishra Ponneri Chandrababu Ravikumar

Published in: Chemical communications (Cambridge, England) (2022)

A Rh-catalyzed C(sp 2 )-H propenylation has been reported by taking N -allyl benzimidazole as an allylamine congener. This transformation has been observed for the first time, where a tandem process of C-H allylation followed by alkene isomerization delivers a highly stereoselective trans -propenylated product. Detailed mechanistic studies including the characterization of rhodacycle-intermediates have been conducted to understand the mechanism.

Keyphrases

room temperature
molecular docking
case control
ionic liquid
transition metal
electron transfer