Amphiphilic methyleneamino synthon through organic dye catalyzed-decarboxylative aminoalkylation

被引:88
作者
Chen, Li [1 ]
Chao, Chin Sheng [2 ]
Pan, Yuanhang [1 ]
Dong, Sheng [1 ]
Teo, Yew Chin [1 ]
Wang, Jian [1 ]
Tan, Choon-Hong [2 ]
机构
[1] Natl Univ Singapore, Dept Chem, Singapore 117543, Singapore
[2] Nanyang Technol Univ, Div Chem & Biol Chem, Sch Phys & Math Sci, Singapore 63737, Singapore
关键词
C-H ARYLATION; PHOTOREDOX CATALYSIS; DUAL CATALYSIS; FUNCTIONALIZATION; RADICALS; STRATEGY; ALKYNYLATION;
D O I
10.1039/c3ob41091a
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The utilization of a photo-induced synthon generated from N-phenyl glycine by an organic dye and visible light irradiation is disclosed. The intermediate could be coupled with either a radical or a nucleophile in a simple operation to afford several natural product-like compounds.
引用
收藏
页码:5922 / 5925
页数:4
相关论文
共 47 条
  • [1] Visible-Light Photoredox Catalysis: Aza-Henry Reactions via C-H Functionalization
    Condie, Allison G.
    Gonzalez-Gomez, Jose C.
    Stephenson, Corey R. J.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (05) : 1464 - +
  • [2] Photoredox-Initiated α-Alkylation of Imines through a Three-Component Radical/Cationic Reaction
    Courant, Thibaut
    Masson, Geraldine
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (02) : 423 - 427
  • [3] Catalytic Asymmetric α-Acylation of Tertiary Amines Mediated by a Dual Catalysis Mode: N-Heterocyclic Carbene and Photoredox Catalysis
    DiRocco, Daniel A.
    Rovis, Tomislav
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (19) : 8094 - 8097
  • [4] THE PHOTOCHEMICAL-SYNTHESIS OF FINE CHEMICALS WITH SUNLIGHT
    ESSER, P
    POHLMANN, B
    SCHARF, HD
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1994, 33 (20): : 2009 - 2023
  • [5] Visible light photoredox organocatalysis: a fully transition metal-free direct asymmetric α-alkylation of aldehydes
    Fidaly, Kassim
    Ceballos, Claire
    Falguieres, Annie
    Veitia, Maite Sylla-Iyarreta
    Guy, Alain
    Ferroud, Clotilde
    [J]. GREEN CHEMISTRY, 2012, 14 (05) : 1293 - 1297
  • [6] Selective trifluoromethylation and alkynylation of tetrahydroisoquinolines using visible light irradiation by Rose Bengal
    Fu, Weijun
    Guo, Wenbo
    Zou, Guanglong
    Xu, Chen
    [J]. JOURNAL OF FLUORINE CHEMISTRY, 2012, 140 : 88 - 94
  • [7] Photoinduced azidohydroperoxidation of myrtenyl hydroperoxide with semiconductor particles and lucigenin as PET-catalysts
    Griesbeck, Axel G.
    Reckenthaeler, Melissa
    Uhlig, Johannes
    [J]. PHOTOCHEMICAL & PHOTOBIOLOGICAL SCIENCES, 2010, 9 (06) : 775 - 778
  • [8] Metal-Free, Visible-Light-Mediated Direct C-H Arylation of Heteroarenes with Aryl Diazonium Salts
    Hari, Durga Prasad
    Schroll, Peter
    Koenig, Burkhard
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (06) : 2958 - 2961
  • [9] Functionalization of Organic Molecules by Transition-Metal-Catalyzed C(sp3)-H Activation
    Jazzar, Rodolphe
    Hitce, Julien
    Renaudat, Alice
    Sofack-Kreutzer, Julien
    Baudoin, Olivier
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (09) : 2654 - 2672
  • [10] The Reaction of Tertiary Anilines with Maleimides under Visible Light Redox Catalysis
    Ju, Xuhui
    Li, Dianjun
    Li, Weifei
    Yu, Wei
    Bian, Fengling
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2012, 354 (18) : 3561 - 3567