Litcius/Paper detail

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

Pengqing Ye, Yinlin Shao, Xuanzeng Ye, Fangjun Zhang, Renhao Li, Jiani Sun, Beihang Xu, Jiuxi Chen

2020Organic Letters64 citationsDOI

Abstract

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.

Topics & Concepts

ChemistryHomolepticTrimethylsilylHydroborationCatalysisOrganic chemistryNitroHomogeneousProtonolysisLanthanideCombinatorial chemistryYttriumMedicinal chemistryMetalIonOxideThermodynamicsAlkylPhysicsAdvanced Synthetic Organic ChemistryAsymmetric Hydrogenation and CatalysisOrganoboron and organosilicon chemistry