Vinylic Trifluoromethylselenolation via Pd‐Catalyzed C−H Activation. Issue 63 (2nd September 2022) - de Zordo‐Banliat, Arnaud
Abstract: Trifluorometylselenolation via C−H activation is barely described in literature. In particular, no such vinylic functionalization has been yet described. Herein, a palladium‐catalyzed 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 α‐substituted compounds whatever the substituents and a microwave activation can be used to accelerate the reaction. With β‐substituted substrates lower yields, but still satisfactory, are obtained. This methodology was also successfully extended to other fluoroalkylselenyl groups. Abstract : Trifluoromethylselenolation of vinylic substrates was performed through a palladium‐catalyzed C−H activation. This reaction was based on the use of 5‐methoxy‐8‐amino‐quinoline as directing group and trifluoromethyl tolueneselenosulfonate as trifluoromethylselenolating reagent. This method was also extended to fluoroalkylselenolation reactions.