Rapid, Mild, and Selective Ketone and Aldehyde Hydroboration/Reduction Mediated by a Simple Lanthanide Catalyst

Rapid, clean hydroboration of ketones and aldehydes with HBpin is achieved using the homoleptic rare-earth catalyst La[N-(SiMe-3)-2](3) (La-NTMS). The reaction employs low catalyst loadings (0.01-1 mol % La-NTMS), proceeds rapidly (>99% in 5 min) at 25 degrees C, and is moderately air-tolerant. Additionally, this hydroboration has good functional group compatibility, including halides, nitro groups, and nitriles, and is exclusively carbonyl-selective in the presence of alkenes and alkynes.