Palladium-Catalyzed Oxidative Cross-Coupling Reaction of Arylboronic Acids with Diazoesters for Stereoselective Synthesis of (E)-α,β-Diarylacrylates

被引:70
作者
Tsoi, Yuk-Tai
Zhou, Zhongyuan
Chan, Albert S. C.
Yu, Wing-Yiu [1 ]
机构
[1] Hong Kong Polytech Univ, Dept Appl Biol & Chem Technol, State Key Lab Chiosci, Kowloon, Hong Kong, Peoples R China
关键词
ALPHA-DIAZOCARBONYL COMPOUNDS; CARBENE INSERTION; BIOLOGICAL EVALUATION; ARYLATION;
D O I
10.1021/ol101796t
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A Pd-catalyzed oxidative cross-coupling reaction of arylboronic acids with alpha-diazoesters was achieved using molecular oxygen as the sole reoxidant, and E-alpha,beta-diarylacrylates were obtained in good yields and >20 1 E-to-Z selectivity
引用
收藏
页码:4506 / 4509
页数:4
相关论文
共 36 条
  • [1] Formation of a vinyliminium palladium complex by C-C coupling in vinylcarbene palladium aryl complexes
    Albéniz, AC
    Espinet, P
    Pérez-Mateo, A
    Nova, A
    Ujaque, G
    [J]. ORGANOMETALLICS, 2006, 25 (05) : 1293 - 1297
  • [2] Aryl palladium carbene complexes and carbene-aryl coupling reactions
    Albéniz, AC
    Espinet, P
    Manrique, R
    Pérez-Mateo, A
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2005, 11 (05) : 1565 - 1573
  • [3] BAILUENGA J, 2009, NAT CHEM, V1, P494
  • [4] Pd-catalyzed cross-coupling reactions with carbonyls:: Application in a very efficient synthesis of 4-aryltetrahydropyridines
    Barluenga, Jose
    Tomas-Gamasa, Maria
    Moriel, Patricia
    Amar, Fernando
    Valdes, Carlos
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (16) : 4792 - 4795
  • [5] N-tosylhydrazones as reagents for cross-coupling reactions:: A route to polysubstituted olefins
    Barluenga, José
    Moriel, Patricia
    Valdes, Carlos
    Aznar, Fernando
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (29) : 5587 - 5590
  • [6] CoMFA, synthesis, and pharmacological evaluation of (E)-3-(2-carboxy-2-arylvinyl)-4,6-dichloro-1H-indole-2-carboxylic acids:: 3-[2-(3-Aminophenyl)-2-carboxyvinyl)-4,6-dichloro-1H-indole-2-carboxylic acid, a potent selective glycine-site NMDA receptor antagonist
    Baron, BM
    Cregge, RJ
    Farr, RA
    Friedrich, D
    Gross, RS
    Harrison, BL
    Janowick, DA
    Matthews, D
    McCloskey, TC
    Meikrantz, S
    Nyce, PL
    Vaz, R
    Metz, WA
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 2005, 48 (04) : 995 - 1018
  • [7] Synthesis of benzo analogs of oxoarcyriaflavins and caulersine
    Bourderioux, Aurelie
    Routier, Sylvain
    Beneteau, Valerie
    Merour, Jean-Yves
    [J]. TETRAHEDRON, 2007, 63 (38) : 9465 - 9475
  • [8] CATIONIC PLATINUM(II)-CARBYL OR PALLADIUM(II)-CARBYL COMPLEXES AND UNSATURATED SUBSTRATES - A FACILE WAY TO C-C BOND FORMATION
    DEFELICE, V
    CUCCIOLITO, ME
    DERENZI, A
    RUFFO, F
    TESAURO, D
    [J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1995, 493 (1-2) : 1 - 11
  • [9] DEMEIJERE A, 2004, METLA CATALIZED CROS
  • [10] Palladium-catalyzed carbene insertion and trapping with carbon nucleophiles
    Devine, Sean K. J.
    Van Vranken, David L.
    [J]. ORGANIC LETTERS, 2008, 10 (10) : 1909 - 1911