Visible light bromide catalysis for oxazoline, pyrrolidine, and dihydrooxazine syntheses via Csp3-H functionalizations

Chem Commun (Camb). 2021 Oct 7;57(80):10387-10390. doi: 10.1039/d1cc04588a.


A catalytic benzylic Csp3-H functionalization protocol is described here. This visible light-mediated process is centered on the utilization of a bromide catalyst and oxidant to generate a nitrogen (N)-centered radical for a site-selective hydrogen atom transfer (HAT) process. This strategy enabled the unconventional syntheses of a number of N-heterocycles dependent on the amide identity. We also discovered a nucleophilicity-dependent kinetic resolution for stereochemical differentiation of Csp3-H bonds that enabled the stereoselective synthesis of cis- and trans-oxazolines.