N-Allylbenzimidazole as a strategic surrogate in Rh-catalyzed stereoselective trans-propenylation of aryl C(sp2)-H bond

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.

Automated summary

This article reports a novel reaction method for the highly stereoselective C(sp(2))-H propenylation using N-allyl benzimidazole as a catalyst. Detailed mechanistic studies were conducted to understand the reaction mechanism.