Fluorescent Dye/Nickel Synergistic Catalytic Decarboxylative Carbonylation Reaction

The decarboxylative carbonylation of alpha-amino acids was carried out with N-benzoyl succinimide as the carbonylation reagent under the synergistic catalysis of fluorescent dye/nickel catalysts. In this reaction, 16 kinds of alpha-amino ketone-containing derivatives were synthesized with good yields (up to 78%), and the light conversion efficiency was up to 3.25 X 10(-1) mmol/(kW.h). In addition, the possible mechanism of the photocatalytic reaction was proposed: alpha-amino carboxylic acid was catalyzed by visible light to form alpha-amino alkyl radicals, which entered the nickel catalytic cycle and produced alpha-amino ketone target compound via oxidation addition and reduction elimination process. The reactions could generate a variety of alpha-amino ketones with broad substrate scope under mild conditions and might have widespread use in synthesis of alpha-amino ketone-containing drug molecules and peptide modifications.