Decarboxylative Aminomethylation of Aryl- and Vinylsulfonates through Combined Nickel- and Photoredox-Catalyzed Cross-Coupling

被引：84
作者：
Fan, Lulu [1 ]
Jia, Jiaqi [1 ]
Hou, Hong [1 ]
Lefebvre, Quentin [1 ]
Rueping, Magnus [1 ,2 ]
机构：
[1] Rhein Westfal TH Aachen, Inst Organ Chem, Landoltweg 1, D-52074 Aachen, Germany
[2] KAUST, KAUST Catalysis Ctr KCC, Thuwal 239556900, Saudi Arabia
来源：
CHEMISTRY-A EUROPEAN JOURNAL | 2016年 / 22卷 / 46期
基金：
欧洲研究理事会;
关键词：
amino acids; cross-coupling; decarboxylation; nickel catalysis; photoredox catalysis; SINGLE-ELECTRON TRANSMETALATION; VISIBLE-LIGHT PHOTOCATALYSIS; O BOND ACTIVATION; C-H BONDS; DUAL CATALYSIS; MERGING PHOTOREDOX; PHENOL DERIVATIVES; ORGANIC-SYNTHESIS; CARBOXYLIC-ACIDS; METAL CATALYSIS;
D O I：
10.1002/chem.201604452
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A mild approach for the decarboxylative aminomethylation of aryl sulfonates by the combination of photoredox and nickel catalysis through C-O bond cleavage is described for the first time. A wide range of aryl triflates as well as aryl mesylates, tosylates and alkenyl triflates afford the corresponding products in good to excellent yields.
引用
收藏
页码：16437 / 16440
页数：4
相关论文
共 73 条
  • [1] Visible Light Photoredox Cross-Coupling of Acyl Chlorides with Potassium Alkoxymethyltrifluoroborates: Synthesis of α-Alkoxyketones
    Amani, Javad
    Sodagar, Esmat
    Molander, Gary A.
    [J]. ORGANIC LETTERS, 2016, 18 (04) : 732 - 735
  • [2] [Anonymous], 2015, ANGEW CHEM-GER EDIT
  • [3] [Anonymous], 2014, ANGEW CHEM-GER EDIT
  • [4] [Anonymous], 2016, ANGEW CHEM
  • [5] Photoredox Catalysis in Nickel-Catalyzed Cross-Coupling
    Cavalcanti, Livia N.
    Molander, Gary A.
    [J]. TOPICS IN CURRENT CHEMISTRY, 2016, 374 (04)
  • [6] Amphiphilic methyleneamino synthon through organic dye catalyzed-decarboxylative aminoalkylation
    Chen, Li
    Chao, Chin Sheng
    Pan, Yuanhang
    Dong, Sheng
    Teo, Yew Chin
    Wang, Jian
    Tan, Choon-Hong
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2013, 11 (35) : 5922 - 5925
  • [7] 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.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (27) : 7929 - 7933
  • [8] Colacot TJ, 2015, RSC CATAL SER, P1
  • [9] Corce V., 2015, Angewandte Chemie, V127, P11576, DOI DOI 10.1021/ol5021477
  • [10] Silicates as Latent Alkyl Radical Precursors: Visible-Light Photocatalytic Oxidation of Hypervalent Bis-Catecholato Silicon Compounds
    Corce, Vincent
    Chamoreau, Lise-Marie
    Derat, Etienne
    Goddard, Jean-Philippe
    Ollivier, Cyril
    Fensterbank, Louis
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (39) : 11414 - 11418
12345678