Radical coupling of β-ketoesters and amides promoted by Brønsted/Lewis acids
Joshua L. Zhu, Stephen W. Laws, Michael J. Rourke, Karl A. Scheidt
Abstract
Recent advances in photocatalysis have enabled radical methods with complementary chemoselectivity to established two electron bond forming approaches. While this radical strategy has previously been limited to substrates with favorable redox potentials, Brønsted/Lewis acid activation has emerged as a means of facilitating otherwise difficult reductions. We report herein our investigations into the Lewis acid-promoted redox activation of β-ketocarbonyls in a model photocatalytic radical alkylation reaction. Rapid evaluation of substrates and reactions conditions was achieved by high throughput experimentation using 96-well plate photoreactors.
Topics & Concepts
ChemoselectivityLewis acids and basesPhotocatalysisBrønsted–Lowry acid–base theoryChemistryRedoxCatalysisAlkylationPhotochemistryCombinatorial chemistryLewis acid catalysisOrganic chemistryRadical Photochemical ReactionsSulfur-Based Synthesis TechniquesCatalytic C–H Functionalization Methods