Titanium-Mediated Reduction of Carboxamides to Amines with Borane–Ammonia
P. Veeraraghavan Ramachandran, Abdulkhaliq A. Alawaed, Aman Singh
Abstract
In this study, the successful titanium tetrachloride-catalyzed reduction of aldehydes, ketones, carboxylic acids, and nitriles with borane-ammonia was extended to the reduction (deoxygenation) of a variety of aromatic and aliphatic pri-, sec- and tert-carboxamides, by changing the stoichiometry of the catalyst and reductant. The corresponding amines were isolated in good to excellent yields, following a simple acid-base workup.
Topics & Concepts
DeoxygenationChemistryCatalysisBoraneAmmoniaAmmonia boraneStoichiometryTitanium tetrachlorideOrganic chemistryTitaniumCombinatorial chemistryDehydrogenationAsymmetric Hydrogenation and CatalysisChemical Synthesis and AnalysisOrganoboron and organosilicon chemistry