Vinylic Trifluoromethylselenolation via Pd‐Catalyzed C−H Activation. Issue 63 (2nd September 2022)

• Record Type: Journal Article
• Authors: de Zordo‐Banliat, Arnaud; Grollier, Kevin; Vigier, Jordan; Jeanneau, Erwann; Dagousset, Guillaume; Pegot, Bruce; Magnier, Emmanuel; Billard, Thierry
• Is Part Of: Chemistry. Volume 28:Issue 63(2022)
• Page Start: n/a
• Page End: n/a
• Publication Date: 2022-09-02
• Subjects: C−H functionalization -- fluorine -- selenium -- trifluoromethylselenolation -- trifluoromethylselenosulfonate; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.202202299
• Languages: English
• ISSNs: 0947-6539

Abstract

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.