Phosphine-Catalyzed Anti-Hydroboration of Internal Alkynes.

Trialkylphosphine organocatalysts have enabled regioselective anti-hydroboration of internal alkynes with pinacolborane reagents to provide ( E)-disubstituted alkenylboronate compounds. The alkenylboronate can be used for derivatizations, such as protodeborylation, Suzuki-Miyaura coupling, conjugate reduction, and Diels-Alder reactions.