hydroborationamination

Hydroboration-amination is a chemical reaction that involves the addition of a boron-nitrogen bond across a carbon-carbon double or triple bond. This process typically results in the formation of vicinal aminoalkylboranes or related derivatives. The reaction is often catalyzed by transition metals such as rhodium, iridium, or copper. The mechanism usually proceeds through a concerted addition of the B-N bond to the unsaturated system, similar to hydroboration. The regioselectivity of the reaction can be influenced by the electronic and steric properties of the substrate and the catalyst. Following the initial hydroboration-amination step, the resulting organoborane intermediate can be further functionalized. Common transformations include oxidation to form vicinal amino alcohols or protonolysis to yield amines. Hydroboration-amination offers a synthetic route to valuable nitrogen-containing compounds, finding applications in organic synthesis for the preparation of pharmaceuticals, agrochemicals, and other fine chemicals. The reaction's ability to control stereochemistry, particularly enantioselectivity when chiral catalysts are employed, makes it a powerful tool for asymmetric synthesis.