Decarboxylative Arylation of α-Amino Acids via Photoredox Catalysis: A One-Step Conversion of Biomass to Drug Pharmacophore

被引：461
|
作者：
Zuo, Zhiwei [1 ]
MacMillan, David W. C. [1 ]
机构：
[1] Princeton Univ, Merck Ctr Catalysis, Princeton, NJ 08544 USA
来源：
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2014年 / 136卷 / 14期
关键词：
ELECTROCHEMICAL OXIDATION; COORDINATION-COMPOUNDS; IRIDIUM(III); RADICALS; LIGHT; TRANSFORMATIONS; COMPLEXES; ALDEHYDES; SALTS;
D O I：
10.1021/ja501621q
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
The direct decarboxylative arylation of alpha-amino acids has been achieved via visible light-mediated photoredox catalysis. This method offers rapid entry to prevalent benzylic amine architectures from an abundant biomass, specifically alpha-amino acid precursors. Significant substrate scope is observed with respect to both the amino acid and arene components.
引用
收藏
页码：5257 / 5260
页数：4
相关论文
共 50 条
  • [1] Decarboxylative arylation of α-Amino acids via photoredox catalysis: A one-step conversion of biomass to drug pharmacophore
    Macmillan, D.W.C. (dmacmill@princeton.edu), 1600, American Chemical Society (136):
  • [2] Enantioselective Decarboxylative Arylation of α-Amino Acids via the Merger of Photoredox and Nickel Catalysis
    Fu, Gregory C. (gcfu@caltech.edu), 1832, American Chemical Society (138):
  • [3] Enantioselective Decarboxylative Arylation of α-Amino Acids via the Merger of Photoredox and Nickel Catalysis
    Zuo, Zhiwei
    Gong, Huan
    Li, Wei
    Choi, Junwon
    Fu, Gregory C.
    MacMillan, David W. C.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (06) : 1832 - 1835
  • [4] Direct conversion of amino acids to oxetanol bioisosteres via photoredox catalysis
    Reyes, Avelyn Mae V. Delos
    Escobar, Christopher S. Nieves
    Munoz, Alberto
    Huffman, Maya I.
    Tan, Derek S.
    CHEMICAL SCIENCE, 2023, 14 (38) : 10524 - 10531
  • [5] Decarboxylative Fluorination of Aliphatic Carboxylic Acids via Photoredox Catalysis
    Ventre, Sandrine
    Petronijevic, Filip R.
    MacMillan, David W. C.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (17) : 5654 - 5657
  • [6] Metal-free decarboxylative oxygenation of α-amino acids to amide compounds via photoredox catalysis
    Zhu, Rui
    Wang, Yaxin
    Cui, Minshu
    APPLIED CATALYSIS A-GENERAL, 2025, 691
  • [7] Decarboxylative Elimination of N-Acyl Amino Acids via Photoredox/Cobalt Dual Catalysis
    Cartwright, Kaitie C.
    Tunge, Jon A.
    ACS CATALYSIS, 2018, 8 (12): : 11801 - 11806
  • [8] Merging Photoredox and Nickel Catalysis: The Direct Synthesis of Ketones by the Decarboxylative Arylation of -Oxo Acids
    Chu, Lingling
    Lipshultz, Jeffrey M.
    MacMillan, David W. C.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (27) : 7929 - 7933
  • [9] Decarboxylative elimination of carboxylic acids via photoredox/ cobalt dual catalysis
    Cartwright, Kaitie
    Tunge, Jon
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2019, 257
  • [10] Decarboxylative sulfenylation of amino acids via metallaphotoredox catalysis
    Wei, Lidan
    Wu, Chengjuan
    Tung, Chen-Ho
    Wang, Wenguang
    Xu, Zhenghu
    ORGANIC CHEMISTRY FRONTIERS, 2019, 6 (18): : 3224 - 3227
12345