Control of hydroboration of 1-alkynylphosphonates, followed by Suzuki coupling provides regio- and stereospecific synthesis of di-substituted 1-alkenylphosphonates

Hydroboration of 1-alkynylphosphonates can be controlled to place boron on either C1 or C2 of the triple bond by control of reaction conditions. Initial hydroboration occurs on C1 (kinetic product), which can be isomerized to place boron on C2 (thermodynamic product) by extended heating or by use of large amounts of catalyst. Suzuki reaction of the hydroboration products with aryliodides provides a regio- and stereospecific route to disubstituted vinylphosphonates