Catalytic hydroboration of aldehydes and ketones with sodium hydride: Application to chemoselective reduction of aldehydes over ketones

Abstract

Sodium hydride-promoted catalytic hydroboration of aldehydes and ketones with pinacolborane (HBpin) was examined, and 10 mol% of NaH was found to cause the HBpin to participate in hydroboration in a convenient and efficient manner at mild reaction conditions. Further chemoselective hydroboration of aldehyde over ketone functionality was also analyzed. In addition, no hydroboration was observed form ester, acyl chloride, amide, nitrile, alkene, alkyne, alkyl halide and epoxide functional groups indicate that present system (HBpin, NaH) is highly selective for aldehydes and ketones.