Fluoroalkylation–Borylation of Alkynes: An Efficient Method To Obtain (Z)-Tri- and Tetrasubstituted Fluoroalkylated Alkenylboronates

Efficient methods for the synthesis of fluoroalkylated alkenylboronates are very limited, despite their importance in modern organic synthesis. Herein, we report a palladium-catalyzed trans-fluoroalkylation–borylation of alkynes with fluoroalkyl iodides and B2pin2. The reaction tolerates a series of difluoroalkyl iodides and perfluoroalkyl iodides and can enable coupling with a variety of alkynes, including internal and terminal alkynes, with high efficiency, high functional group compatibility, and high regio- and stereoselectivities. Preliminary mechanistic studies reveal that a trans-fluoroalkylated alkenyl iodide is the key intermediate, which subsequently undergoes borylation to produce the trans-fluoroalkylated alkenylboronate.