Palladium-Catalyzed anti-Selective Fluoroalkylboration of Internal and Terminal Alkynes.

A Pd-catalyzed anti-stereospecific alkyne fluoroalkylboration, including mono-, di-, and perfluoroalkylboration, has been developed with fluoroalkyl halides and diboron reagents. The reaction is effective for both internal and terminal alkynes. It provides straightforward and streamlined access to functionalized 1,2-fluoroalkylboronated alkenes in a highly regio- and stereocontrolled manner. Preliminary studies suggest that this reaction is enabled by the combination of radical alkylation and metal-catalyzed borylation, thus leading to the realization of three-component trans-carboboration of alkynes for the first time.