Π-Π Stacking Complex Induces Three-Component Coupling Reactions To Synthesize Functionalized Amines

Angew Chem Int Ed Engl. 2022 Dec 5;61(49):e202212083. doi: 10.1002/anie.202212083. Epub 2022 Nov 9.

Abstract

π-π stacking and ion-pairing interactions induced the generation of α-amino radicals under the irradiation of visible light without the requirement of an expensive photocatalyst. This strategy enabled the construction of functionalized amines via three-component coupling reactions with broad scope (we report >50 examples with an up to 90 % yield). This synthetic pathway also delivered complex functionalized amines with a very high yield. Quantum chemistry Density Functional Theory (DFT) calculations identified π-π stacked ionic complexes; time-dependent DFT was employed to simulate the absorption spectra, and nudged elastic band (NEB) methodology provided a possible interaction/reaction picture of the selected species.

Keywords: Ionic Complexes; Noncovalent Interactions; Visible Light; α-Amino Radicals.