Palladium-Catalyzed Cross Coupling Reaction of Benzyl Bromides with Diazoesters for Stereoselective Synthesis of (E)-α,β-Diarylacrylates

被引：92
作者：
Yu, Wing-Yiu [1 ]
Tsoi, Yuk-Tai
Zhou, Zhongyuan
Chan, Albert S. C.
机构：
[1] Hong Kong Polytech Univ, Dept Appl Biol & Chem Technol, Kowloon, Hong Kong, Peoples R China
来源：
ORGANIC LETTERS | 2009年 / 11卷 / 02期
关键词：
C-H INSERTION; ALPHA-DIAZOCARBONYL COMPOUNDS; CARBENE INSERTION; BIOLOGICAL EVALUATION; HECK REACTION; COMPLEXES; CYCLOPROPANATION; HALIDES; BOND; FUNCTIONALIZATION;
D O I：
10.1021/ol8026076
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A Pd-catalyzed cross-coupling reaction of benzyl bromides with alpha-aryldiazoesters is described, and E-alpha,beta-diarylacrylates were obtained in good yields and excellent E-to-Z selectivity (>20:1).
引用
收藏
页码：469 / 472
页数：4
相关论文
共 41 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] Albéniz AC, 2002, ANGEW CHEM INT EDIT, V41, P2363, DOI 10.1002/1521-3773(20020703)41:13<2363::AID-ANIE2363>3.0.CO
  • [4] 2-9
  • [5] [Anonymous], EL C TRENDS ORG CHEM
  • [6] 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
  • [7] The heck reaction as a sharpening stone of palladium catalysis
    Beletskaya, IP
    Cheprakov, AV
    [J]. CHEMICAL REVIEWS, 2000, 100 (08) : 3009 - 3066
  • [8] Palladium-catalyzed reaction of allyl halides with α-diazocarbonyl compounds
    Chen, Shufeng
    Wang, Jianbo
    [J]. CHEMICAL COMMUNICATIONS, 2008, (35) : 4198 - 4200
  • [9] Ruthenium porphyrin catalyzed intramolecular carbenoid C-H insertion. Stereloselective synthesis of cis-disubstituted oxygen and nitrogen heterocycles
    Cheung, WH
    Zheng, SL
    Yu, WY
    Zhou, GC
    Che, CM
    [J]. ORGANIC LETTERS, 2003, 5 (14) : 2535 - 2538
  • [10] Ruthenium-catalyzed stereoselective intramolecular carbenoid C-H insertion for β- and γ-lactam formations by decomposition of α-diazoacetamides
    Choi, MKW
    Yu, WY
    Che, CM
    [J]. ORGANIC LETTERS, 2005, 7 (06) : 1081 - 1084
12345