Photoredox Catalyzed Trifluoromethyl Radical-Triggered Trifunctionalization of 5-Hexenenitriles via Cyano Migration

A photoredox catalyzed trifluoromethyl radical-triggered trifunctionalization of 5-hexenenitriles via cyano group migration is reported. The cyano group migration is of high chemo-selectivity even in the presence of aryl or heteroaryl groups as competitors. This protocol provides a facile access to a broad scope of CF3-containing compounds with high molecular complexity and functional group diversity. The success of gram-scale reaction and the versatility of products in derivative synthesis illustrate the potential value of this transformation in synthetic chemistry.

Automated summary

In this study, a photoredox catalyzed trifluoromethyl radical-triggered trifunctionalization of 5-hexenenitriles via cyano group migration is reported. The migration of the cyano group shows high chemo-selectivity even in the presence of aryl or heteroaryl groups as competitors. This protocol provides a simple access to CF3-containing compounds with high molecular complexity and functional group diversity. The successful gram-scale reaction and the versatility of the products in derivative synthesis illustrate the potential value of this transformation in synthetic chemistry.