A Mechanistic Alternative for the Intramolecular Hydroboration of Homoallylic Amine and Phosphine Borane Complexes

Abstract
Intramolecular hydroboration is demonstrated starting from homoallylic amine boranes upon activation by iodine. The process involves a B-iodoborane complex as the intermediate and may occur via internal displacement of iodide by the alkene to generate a cationic borane-alkene π-complex on the way to hydroboration products. The reaction can be carried out using a catalytic amount of iodine.