The Coupling of Tertiary Amines with Acrylate Derivatives via Visible-Light Photoredox Catalysis

被引:84
作者
Dai, Xiaojun [1 ]
Cheng, Dongping [2 ]
Guan, Baochuan [1 ]
Mao, Wenjuan [1 ]
Xu, Xiaoliang [1 ]
Li, Xiaonian [1 ]
机构
[1] Zhejiang Univ Technol, Coll Chem Engn, Inst Ind Catalysis, Hangzhou 310014, Zhejiang, Peoples R China
[2] Zhejiang Univ Technol, Coll Pharmaceut Sci, Hangzhou 310014, Zhejiang, Peoples R China
关键词
ALPHA-AMINOALKYL RADICALS; C-H FUNCTIONALIZATION; DUAL CATALYSIS; AEROBIC OXIDATION; PHOTOCATALYSIS; ALKENES; BONDS; PHOTOOXIDATION; EFFICIENT; ARYLATION;
D O I
10.1021/jo501097b
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Catalyzed by Ru(bpy)(3)(BF4)(2), the photoredox coupling of tertiary amines with acrylate derivatives including Baylis-Hillman adducts under visible light irradiation was successfully established. The scope of the substrates was broad, and thus an array of gamma-aminobutyric ester derivatives was obtained in moderate to good yields.
引用
收藏
页码:7212 / 7219
页数:8
相关论文
共 86 条
  • [1] Recent Contributions from the Baylis-Hillman Reaction to Organic Chemistry
    Basavaiah, Deevi
    Reddy, Bhavanam Sekhara
    Badsara, Satpal Singh
    [J]. CHEMICAL REVIEWS, 2010, 110 (09) : 5447 - 5674
  • [2] Bergonzini G, 2014, CHEM SCI, V5, P112, DOI [10.1039/c3sc52265b, 10.1039/C3SC52265B]
  • [3] Porphycene-mediated photooxidation of benzylamines by visible light
    Berlicka, Anna
    Koenig, Burkhard
    [J]. PHOTOCHEMICAL & PHOTOBIOLOGICAL SCIENCES, 2010, 9 (10) : 1359 - 1366
  • [4] TRIS(2,2'-BIPYRIDINE)RUTHENIUM(II) DICHLORIDE HEXAHYDRATE
    BROOMHEAD, JA
    YOUNG, CG
    [J]. INORGANIC SYNTHESES, 1990, 28 : 338 - 340
  • [5] Visible-Light-Promoted C-C Bond Cleavage: Photocatalytic Generation of Iminium Ions and Amino Radicals
    Cai, Shunyou
    Zhao, Xinyang
    Wang, Xinbo
    Liu, Qisong
    Li, Zigang
    Wang, David Zhigang
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (32) : 8050 - 8053
  • [6] Direct sp3 C-H bond activation adjacent to nitrogen in heterocycles
    Campos, Kevin R.
    [J]. CHEMICAL SOCIETY REVIEWS, 2007, 36 (07) : 1069 - 1084
  • [7] Ciamician G, 1912, Science, V36, P385, DOI 10.1126/science.36.926.385
  • [8] 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 - +
  • [9] 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
  • [10] Friedel-Crafts Amidoalkylation via Thermolysis and Oxidative Photocatalysis
    Dai, Chunhui
    Meschini, Francesco
    Narayanam, Jagan M. R.
    Stephenson, Corey R. J.
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (09) : 4425 - 4431