Visible-Light-Driven C(sp <sup>3</sup> )–H Bond Carboxylation of Benzyl Amines with CO <sub>2</sub> for the Synthesis of α-Amino Acids
Wenwen Cui, Bin Li, Baiquan Wang
Abstract
α-Amino acids are vital structural motifs in both bioactive compounds and synthetic building blocks. However, the photocatalytic synthesis of α-amino acids directly from C(sp 3 )–H bonds and CO 2 is a long-standing challenge. Here we report a visible-light-driven C(sp 3 )–H bond carboxylation of benzylamine with CO 2 to synthesize substituted arylglycines. This reaction has mild reaction conditions, good functional group tolerance, and a wide substrate scope. Mechanistic studies show that carbon radicals and carbon anions as the key intermediates may be generated through a consecutive photoinduced electron transfer process.
Topics & Concepts
ChemistryCarboxylationBenzylamineSubstrate (aquarium)RadicalElectron transferCarbon fibersFunctional groupDouble bondOrganic chemistryPhotocatalysisCombinatorial chemistryReinforced carbon–carbonCarbon monoxideTriple bondPhotochemistryYield (engineering)Reaction intermediateCarbon–carbon bondMedicinal chemistryCarbonylationCarbon atomOrganic synthesisCatalysisMoleculeReaction conditionsAmino acidGroup (periodic table)StereochemistryReactive intermediateCarbon dioxide utilization in catalysisRadical Photochemical ReactionsCO2 Reduction Techniques and Catalysts