Palladium-Catalyzed Chemo- and Regioselective 1,2-Alkynylboration of Unactivated Aliphatic Alkenes

A palladium-catalyzed 1,2-alkynylboration of unactivated alkenes with alkynyl bromides and B₂pin₂ is reported. This method efficiently delivers valuable β-boryl-γ-alkynyl and γ-boryl-δ-alkynyl amides with exclusive chemo- and regioselectivities. The reaction accommodates both terminal and internal alkenes, including sterically hindered substrates, and proceeds under mild conditions. Synthetic utility is demonstrated through gram-scale synthesis and diverse downstream transformations of the boryl-alkyne products.