Catalytic Hydroboration of Aldehydes, Ketones, and Alkenes Using Potassium Carbonate: A Small Key to Big Transformation.

An efficient transition-metal-free protocol for the hydroboration of aldehydes and ketones (reduction) was developed. The hydroboration of a wide range of aldehydes and ketones with pinacolborane (HBpin) under the K(2)CO(3) catalyst has been studied. The reaction system is practical and reliable and proceeds under extremely mild and operationally simple conditions. No prior preparation of the complex metal catalyst was required, and hydroboration occurred stoichiometrically. Further, the chemoselective reduction of aldehydes over ketones was carried out. Moreover, we demonstrated the use of K(2)CO(3) as an efficient catalyst for the hydroboration of alkenes. The operational simplicity, inexpensive and transition-metal-free catalyst, and the applicability to gram-scale synthesis strengthen its potential applications for hydroboration (reduction) at an industrial scale.