Physics

Organic chemistry

Lanthanide

Combinatorial chemistry

Trimethylsilyl

Protonolysis

Yttrium

Homogeneous

Catalysis

Medicinal chemistry

Hydroboration

Chemistry

Nitro

Homoleptic

Oxide

Alkyl

Metal

Thermodynamics

Organic Letters

Homoleptic lanthanide complex Y[N(TMS)2]3 is an efficient homogeneous catalyst for the hydroboration reduction of secondary amides and tertiary amides to corresponding amines. A series of amides containing different functional groups such as cyano, nitro, and vinyl groups were found to be well-tolerated. This transformation has also been nicely applied to the synthesis of indoles and piribedil. Detailed isotopic labeling experiments, control experiments, and kinetic studies provided cumulative evidence to elucidate the reaction mechanism.

Homoleptic Bis(trimethylsilyl)amides of Yttrium Complexes Catalyzed Hydroboration Reduction of Amides to Amines