Vinylic Trifluoromethylselenolation via Pd-Catalyzed C-H Activation

Trifluorometylselenolation via C-H activation is barely described in literature. In particular, no such vinylic functionalization has been yet described. Herein, a palladiumcatalyzed trifluoromethylselenolation of vinylic C-H bonds is described. The 5-methoxy-8-aminoquinoline has been used as auxiliary directing group to perform this reaction. The reaction gives excellent yields with a-substituted compounds whatever the substituents and a microwave activation can be used to accelerate the reaction. With beta-substituted substrates lower yields, but still satisfactory, are obtained. This methodology was also successfully extended to other fluoroalkylselenyl groups.

Automated summary

This article describes a palladium-catalyzed trifluoromethylselenolation reaction of vinylic C-H bonds. The reaction utilizes 5-methoxy-8-aminoquinoline as an auxiliary directing group, and gives excellent yields regardless of the nature of the substituents.