Deoxygenation of Primary Amides to Amines with Pinacolborane Catalyzed by Ca[N(SiMe<sub>3</sub>)<sub>2</sub>]<sub>2</sub>(THF)<sub>2</sub>
Chong Wen Yu, Chenjun Guo, Linhong Jiang, Mingliang Gong, Yunjie Luo
Abstract
Deoxygenative reduction of amides is a challenging but favorable synthetic method of accessing amines. In the presence of a catalytic amount of Ca[N(SiMe3)2]2(THF)2, pinacolborane (HBpin) could efficiently reduce a broad scope of amides, primary amides in particular, into corresponding amines. Functional groups and heteroatoms showed good tolerance in this process of transformation, and a plausible reaction mechanism was proposed.
Topics & Concepts
ChemistryDeoxygenationHeteroatomCatalysisPrimary (astronomy)Medicinal chemistryScope (computer science)Organic chemistryCombinatorial chemistryComputer scienceAstronomyPhysicsRing (chemistry)Programming languageOrganoboron and organosilicon chemistryAdvanced Synthetic Organic ChemistryAsymmetric Hydrogenation and Catalysis