Catalytic hydroboration of aldehydes, ketones, alkynes and alkenes initiated by NaOH

Commercially available NaOH powder is shown to be an efficient transition-metal-free initiator for the catalytic hydroboration of aldehydes, ketones, alkynes and alkenes with HBpin and 9-BBN under mild conditions. Combined experimental and theoretical studies suggest that the catalytically active species is a boron hydride generated in situ from the reaction mixture.