Palladium-Catalyzed Heck-Type Coupling of Allyl Esters: β-Hydride versus β-Acetoxy Elimination

被引:51
|
作者
Pan, Delin [1 ]
Jiao, Ning [1 ]
机构
[1] Peking Univ, Sch Pharmaceut Sci, State Key Lab Nat & Biomimet Drugs, Beijing 100191, Peoples R China
基金
美国国家科学基金会;
关键词
transition-metal catalysis; allyl esters; Heck-type reactions; beta-eliminations; couplings; ELECTRON-RICH OLEFINS; C-H BOND; ARYL HALIDES; ARYLBORONIC ACIDS; ROOM-TEMPERATURE; BASE-FREE; DECARBOXYLATIVE OLEFINATION; AROMATIC-SUBSTITUTION; VERSATILE CATALYST; HIGHLY EFFICIENT;
D O I
10.1055/s-0030-1258083
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
This account presents recent progress in palladium-catalyzed Heck-type reactions of allyl esters with aryl halides, arylmetallic reagents, or arenes. Many improvements have been achieved to control the regioselectivity of beta-hydride or beta-acetoxy elimination. 1 Introduction 2 Palladium-Catalyzed Heck-Type Coupling of Allyl Esters with Aryl Halides 3 Palladium-Catalyzed Heck-Type Coupling of Allyl Esters with Organometallic Reagents 4 Palladium-Catalyzed Heck-Type Coupling of Allyl Esters with Arenes via Aromatic C-H Activation 5 Other Transition Metal Catalyzed Heck-Type Reactions of Allyl Esters 6 Conclusion
引用
收藏
页码:1577 / 1588
页数:12
相关论文
共 50 条
  • [1] Photoinduced Palladium-Catalyzed Radical Heck-Type Coupling of Cyclobutanone Oxime Esters with Vinyl Arenes
    Yang, Sen
    Cai, Sha-Sha
    Li, Jun-Hua
    Chen, Ming
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2024, 89 (10): : 7243 - 7254
  • [2] Palladium-Catalyzed Oxidative Heck-Type Allylation of β,β-Disubstituted Enones with Allyl Carbonates
    Jin, Weiwei
    Yang, Qin
    Wu, Ping
    Chen, Jiping
    Yu, Zhengkun
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2014, 356 (09) : 2097 - 2102
  • [3] Palladium-Catalyzed Selective Heck-Type Diarylation of Allylic Esters with Aryl Halides Involving a β-OAc Elimination Process
    Liu, Yan
    Yao, Bo
    Deng, Chen-Liang
    Tang, Ri-Yuan
    Zhang, Xing-Guo
    Li, Jin-Heng
    [J]. ORGANIC LETTERS, 2011, 13 (05) : 1126 - 1129
  • [4] Palladium-Catalyzed Heck-Type Coupling via C-N Cleavage
    Fan, Weizheng
    Liu, Faming
    Feng, Bainian
    [J]. SYNLETT, 2015, 26 (09) : 1253 - 1257
  • [5] Palladium-Catalyzed Intermolecular Heck-Type Reaction of Epoxides
    Teng, Shenghan
    Tessensohn, Malcolm E.
    Webster, Richard D.
    Zhou, Jianrong Steve
    [J]. ACS CATALYSIS, 2018, 8 (08): : 7439 - 7444
  • [6] Palladium-Catalyzed Heck-Type Reactions of Alkyl Iodides
    Bloome, Kayla S.
    McMahen, Rebecca L.
    Alexanian, Erik J.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (50) : 20146 - 20148
  • [7] Palladium-Catalyzed Heck-Type Reactions of Allylic Esters with Arylboronic Acids or Potassium Aryltrifluoroborates
    Yao, Bo
    Liu, Yan
    Wang, Meng-Ke
    Li, Jin-Heng
    Tang, Ri-Yuan
    Zhang, Xing-Guo
    Deng, Chen-Liang
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2012, 354 (06) : 1069 - 1076
  • [8] Palladium-Catalyzed Carbonylative Heck-Type Reactions of Alkyl Iodides
    Bloome, Kayla S.
    Alexanian, Erik J.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (37) : 12823 - 12825
  • [9] Palladium-catalyzed intermolecular Heck-type reactions with alkyl iodides
    McMahon, Caitlin
    Alexanian, Erik
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2014, 247
  • [10] Palladium-catalyzed heck-type arylation of acrylate with diaryliodonium salts
    Li, Jian
    Liu, Li
    Zhou, Yun-yao
    Xu, Sai-nan
    [J]. RSC ADVANCES, 2012, 2 (08) : 3207 - 3209