4-Dimethylaminopyridine-Boryl Radical Promoted Regioselective Radical Hydroboration of Electron-Deficient Alkenes

Organoboron compounds have shown significant applications in modern chemical synthesis. Hydroboration of alkenes is among the most widely used methods to access these targets. Herein, a regioselective radical hydroboration reaction of electron-deficient alkenes with 4-dimethylaminopyridine (DMAP)-boryl radical for the synthesis of alpha-boryl functionalized molecules is reported. The reaction features specific alpha-regioselectivity, mild reaction conditions, good functional group tolerance, and broad substrate scope. alpha,beta-Unsaturated esters, amides, carboxylic acid, nitrile, trifluoromethyl molecule, sulfone, and phosphonate are viable substrates for this reaction. The resulting alpha-boryl functionalized molecules can be further transformed to various useful building blocks.