[(PPh<sub>3</sub>)<sub>2</sub>NiCl<sub>2</sub>]-Catalyzed C–N Bond Formation Reaction via Borrowing Hydrogen Strategy: Access to Diverse Secondary Amines and Quinolines
S. N. R. Donthireddy, Vipin K. Pandey, Arnab Rit
Abstract
Commercially available [(PPh3)2NiCl2] was found to be an efficient catalyst for the mono-N-alkylation of (hetero)aromatic amines, employing alcohols to deliver diverse secondary amines, including the drug intermediates chloropyramine (5b) and mepyramine (5c), in excellent yields (up to 97%) via the borrowing hydrogen strategy. This method shows a superior activity (TON up to 10000) with a broad substrate scope at a low catalyst loading of 1 mol % and a short reaction time. Further, this strategy is also successful in accessing various quinoline derivatives following the acceptorless dehydrogenation pathway.
Topics & Concepts
CatalysisDehydrogenationQuinolineChemistryAlkylationCombinatorial chemistrySubstrate (aquarium)Primary (astronomy)HydrogenOrganic chemistryMedicinal chemistryAstronomyOceanographyGeologyPhysicsAsymmetric Hydrogenation and CatalysisCarbon dioxide utilization in catalysisChemical Synthesis and Analysis