Enantioselective Synthesis of <i>N</i>-Benzylic Heterocycles by Ni/Photoredox Dual Catalysis
Caitlin R. Lacker, Travis J. DeLano, Emily P. Chen, Jongrock Kong, Kevin M. Belyk, Tiffany Piou, Sarah E. Reisman
Abstract
An asymmetric cross-coupling of α-N-heterocyclic trifluoroborates with aryl bromides using Ni/photoredox dual catalysis has been developed. This C(sp2)–C(sp3) cross-coupling provides access to pharmaceutically relevant chiral N-benzylic heterocycles in good to excellent enantioselectivity when bioxazolines (BiOX) are used as the chiral ligand. High-throughput experimentation significantly streamlined reaction development by identifying BiOX ligands for further investigation and by allowing for rapid optimization of conditions for new trifluoroborate salts.
Topics & Concepts
ChemistryEnantioselective synthesisCatalysisLigand (biochemistry)Combinatorial chemistryArylPhotoredox catalysisOrganic chemistryPhotocatalysisReceptorBiochemistryAlkylRadical Photochemical ReactionsCatalytic C–H Functionalization MethodsSulfur-Based Synthesis Techniques