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
  • [21] Highly Selective β-Hydride Elimination in Pd-Catalyzed Decarboxylative Heck-Type Reaction
    Huang, Liangbin
    Qi, Ji
    Wu, Xia
    Huang, Kefan
    Jiang, Huanfeng
    [J]. ORGANIC LETTERS, 2013, 15 (10) : 2330 - 2333
  • [22] Palladium-Catalyzed Desulfitative Heck-Type Reaction of Aryl Sulfinic Acids with Alkenes
    Wang, Guan-Wu
    Miao, Tao
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (21) : 5787 - 5790
  • [23] β-hydride elimination in palladium-catalyzed reactions
    Han, XL
    Liu, GX
    Lu, XY
    [J]. CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2005, 25 (10) : 1182 - 1197
  • [24] Palladium-catalyzed Heck-type reaction of oximes with allylic alcohols: synthesis of pyridines and azafluorenones
    Zheng, Meifang
    Chen, Pengquan
    Wu, Wanqing
    Jiang, Huanfeng
    [J]. CHEMICAL COMMUNICATIONS, 2016, 52 (01) : 84 - 87
  • [25] Chelating N-heterocyclic carbene ligands in palladium-catalyzed Heck-type reactions
    Herrmann, WA
    Reisinger, CP
    Spiegler, M
    [J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1998, 557 (01) : 93 - 96
  • [26] Palladium-catalyzed cascade Heck-type cyclization and reductive aminocarbonylation for the synthesis of functionalized amides
    Ren-Rui Xu
    Wen, Dan
    Qi, Xinxin
    Xiao-Feng Wu
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2022, 20 (13) : 2605 - 2608
  • [27] A General Synthesis of Fluoroalkylated Alkenes by Palladium-Catalyzed Heck-Type Reaction of Fluoroalkyl Bromides
    Feng, Zhang
    Min, Qiao-Qiao
    Zhao, Hai-Yang
    Gu, Ji-Wei
    Zhang, Xingang
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (04) : 1270 - 1274
  • [28] Palladium-catalyzed Heck and Suzuki coupling in glycerol
    Wolfson, A.
    Dlugy, C.
    [J]. CHEMICAL PAPERS, 2007, 61 (03): : 228 - 232
  • [29] PALLADIUM-CATALYZED COUPLING OF ALKENYL IODONIUM SALTS WITH OLEFINS - A MILD AND STEREOSELECTIVE HECK-TYPE REACTION USING HYPERVALENT IODINE
    MORIARTY, RM
    EPA, WR
    AWASTHI, AK
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (16) : 6315 - 6317
  • [30] Palladium-Catalyzed Reductive Heck Coupling of Alkenes
    Oxtoby, Lucas J.
    Gurak, John A., Jr.
    Wisniewski, Steven R.
    Eastgate, Martin D.
    Engle, Keary M.
    [J]. TRENDS IN CHEMISTRY, 2019, 1 (06): : 572 - 587