Photoredox-Catalyzed Synthesis of α-Amino Acid Amides by Imine Carbamoylation
Luana Cardinale, Mattis‐Ole W. S. Schmotz, Mikhail O. Konev, Axel Jacobi von Wangelin
Abstract
An operationally simple protocol for the photocatalytic carbamoylation of imines is reported. Easily available, bench-stable 4-amido Hantzsch ester derivatives serve as precursors to carbamoyl radicals that undergo rapid addition to N-aryl imines. The reaction proceeds under blue light irradiation in the presence of the photocatalyst 3DPAFIPN and Brønsted/Lewis acid additives. Mechanistic studies indicated a photoredox mechanism that involves carbamoyl radicals.
Topics & Concepts
ChemistryIminePhotoredox catalysisRadicalPhotocatalysisCatalysisArylLewis acids and basesBrønsted–Lowry acid–base theoryCombinatorial chemistryOrganic chemistryPhotochemistryAlkylSulfur-Based Synthesis TechniquesRadical Photochemical ReactionsSynthesis and Catalytic Reactions