Chinese Journal of Organic Chemistry >
Fluorescent Dye/Nickel Synergistic Catalytic Decarboxylative Carbonylation Reaction
Received date: 2021-10-13
Revised date: 2021-11-24
Online published: 2021-12-02
Supported by
Basic Public Welfare Fund of Zhejiang Province(LGG21H300001); Scientific Research Fund of Zhejiang Provincial Education Department(Y201432790)
The decarboxylative carbonylation of α-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 α-amino ketone-containing derivatives were synthesized with good yields (up to 78%), and the light conversion efficiency was up to 3.25×10–1 mmol/(kW•h). In addition, the possible mechanism of the photocatalytic reaction was proposed: α-amino carboxylic acid was catalyzed by visible light to form α-amino alkyl radicals, which entered the nickel catalytic cycle and produced α-amino ketone target compound via oxidation addition and reduction elimination process. The reactions could generate a variety of α-amino ketones with broad substrate scope under mild conditions and might have widespread use in synthesis of α-amino ketone-containing drug molecules and peptide modifications.
Weiguo Yu , Lingna Wang , Xiaocong Yu , Shuping Luo . Fluorescent Dye/Nickel Synergistic Catalytic Decarboxylative Carbonylation Reaction[J]. Chinese Journal of Organic Chemistry, 2022 , 42(4) : 1216 -1223 . DOI: 10.6023/cjoc202110018
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