Chinese Journal of Organic Chemistry ›› 2022, Vol. 42 ›› Issue (4): 1216-1223.DOI: 10.6023/cjoc202110018 Previous Articles     Next Articles



余卫国a,*(), 王灵娜b, 俞晓聪b, 罗书平b,*()   

  1. a 浙江药科职业大学 药物化学研究所 浙江宁波 315100
    b 浙江工业大学 绿色化学合成技术国家重点实验室培育基地 杭州 310014
  • 收稿日期:2021-10-13 修回日期:2021-11-24 发布日期:2021-12-02
  • 通讯作者: 余卫国, 罗书平
  • 基金资助:
    浙江省基础公益基金(LGG21H300001); 浙江省教育厅科研基金(Y201432790)

Fluorescent Dye/Nickel Synergistic Catalytic Decarboxylative Carbonylation Reaction

Weiguo Yua(), Lingna Wangb, Xiaocong Yub, Shuping Luob()   

  1. a Institute of Medicinal Chemistry, Zhejiang Pharmaceutical Colloge, Ningbo, Zhejiang 315100
    b State Key Laboratory Breeding Base of Green Chemistry-Synthesis Technology, Zhejiang University of Technology, Hangzhou 310014
  • Received:2021-10-13 Revised:2021-11-24 Published:2021-12-02
  • Contact: Weiguo Yu, Shuping Luo
  • 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.

Key words: photocatalysis, nickel catalysis, single electron transfer, decarboxylative coupling reaction