Regioselective 1,2-Alkylboration of Non-conjugated Alkenes Utilizing Diazo Compounds as Alkylating agents Enabled by Pd-catalysis

A modular and straightforward three-component coupling strategy towards structurally complex alkylboranes via a Pd(II)-catalyzed 1,2-alkylboration of non-conjugated alkenes is disclosed herein by employing a diverse range of organoboron nucleophiles and diazo-electrophiles. The reaction proceeds under mild conditions and afforded good to moderate yields and good syn-selectivity in a highly regio- and diastereoselective fashion. The pathway of the transformation involves a carbene migratory insertion using a diazo electrophile as the key mechanistic step. Deborylation and DG-removal further adds an additional importance to the methodology.