Chemoselective Reductive Aminations in Aqueous Nanoreactors Using Parts per Million Level Pd/C Catalysis
Ruchita R. Thakore, Balaram S. Takale, Gianluca Casotti, Eugene S. Gao, Henry S. Jin, Bruce H. Lipshutz
Abstract
Condensation in recyclable water between aldehydes or ketones and amines occurs smoothly within the hydrophobic cores of nanomicelles, resulting in imine formation that is subject to subsequent reduction leading, overall, to reductive amination. This micellar technology enables the synthesis of several types of pharmaceuticals, a new procedure that relies on only 2000 ppm (0.20 mol %) palladium from commercially available Pd/C. A broad range of substrates can be used under mild conditions, leading to high chemical yields of the desired secondary and tertiary amines.
Topics & Concepts
ChemistryReductive aminationNanoreactorAminationCatalysisPalladiumImineAqueous solutionCondensationCombinatorial chemistryOrganic chemistryPhysicsThermodynamicsNanomaterials for catalytic reactionsInnovative Microfluidic and Catalytic Techniques InnovationAsymmetric Hydrogenation and Catalysis