NHC-Silyliumylidene Cation-Catalyzed Hydroboration of Isocyanates with Pinacolborane
Yeow-Chuan Teo, Dexter Loh, Bi‐Xiang Leong, Zhengfeng Zhang, Ming‐Der Su, Cheuk‐Wai So
Abstract
The low-oxidation-state silicon-catalyzed hydroboration of isocyanates with pinacolborane (HBpin) using the NHC-silyliumylidene cation catalyst [(IMe) 2 SiH]I ( 1, IMe =:C{N(Me)C(Me)} 2 ) is described. In the catalysis, the Si lone pair electrons activate isocyanates, and the latter react with HBpin to form N -boryl formamides at room temperature. Catalyst 1 further activates N -boryl formamides at 70 °C, the intermediates of which react with HBpin to form N -boryl methylamines and (pinB) 2 O.
Topics & Concepts
FormamidesChemistryHydroborationCatalysisMedicinal chemistryOrganic chemistryOrganoboron and organosilicon chemistrySynthesis and characterization of novel inorganic/organometallic compoundsN-Heterocyclic Carbenes in Organic and Inorganic Chemistry