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
来源：
SYNLETT | 2010年 / 11期
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
  • [41] Preparation of 2-Amino-5-homoallylfurans via Palladium-Catalyzed Tandem Cycloisomerization/Heck-Type Coupling of Homoallenyl Amides with Allyltrialkylsilanes
    Zhang, Jian
    Wu, Mingchang
    Lu, Wei
    Wang, Shuaifeng
    Zhang, Yan
    Cheng, Cungui
    Zhu, Gangguo
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (20): : 11134 - 11140
  • [42] Palladium-catalyzed carboxylative coupling of allylstannanes and allyl halides
    Franks, RJ
    Nicholas, KM
    [J]. ORGANOMETALLICS, 2000, 19 (08) : 1458 - 1460
  • [43] Synthesis of allyl selenides by palladium-catalyzed decarboxylative coupling
    Waetzig, Shelli R.
    Tunge, Jon A.
    [J]. CHEMICAL COMMUNICATIONS, 2008, (28) : 3311 - 3313
  • [44] Water as a Hydride Source in Palladium-Catalyzed Enantioselective Reductive Heck Reactions
    Kong, Wangqing
    Wang, Qian
    Zhu, Jieping
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (14) : 3987 - 3991
  • [45] Synthesis of pyrazine-bridged diimidazolium salts and their application in palladium catalyzed Heck-type coupling reactions
    Jahnke, Mareike C.
    Hussain, Mukhtiar
    Hupka, Florian
    Pape, Tania
    Ali, Saqib
    Hahn, F. Ekkehardt
    Cavell, Kingsley J.
    [J]. TETRAHEDRON, 2009, 65 (04) : 909 - 913
  • [46] Palladium-catalyzed reductive electrocarboxylation of allyl esters with carbon dioxide
    Jiao, Ke-Jin
    Li, Zhao-Ming
    Xu, Xue-Tao
    Zhang, Li-Pu
    Li, Yi-Qian
    Zhang, Kun
    Mei, Tian-Sheng
    [J]. ORGANIC CHEMISTRY FRONTIERS, 2018, 5 (14): : 2244 - 2248
  • [47] Synthesis of 2,3-Dihydrosiloles via Palladium-Catalyzed Heck-type Arylation of Silacyclopentenes with Aryl Iodides
    Huang, Wei-Sheng
    Ling, Fang-Ying
    Fang, Xiao-Jun
    Cui, Yu-Ming
    Ye, Fei
    Xu, Zheng
    Cao, Jian
    Yang, Hua
    Xu, Li-Wen
    [J]. SYNTHESIS-STUTTGART, 2023, 55 (10): : 1577 - 1585
  • [48] An efficient palladium-catalyzed Heck coupling of aryl chlorides with alkenes
    Yi, CY
    Hua, RM
    [J]. TETRAHEDRON LETTERS, 2006, 47 (15) : 2573 - 2576
  • [49] Ligand effects in palladium-catalyzed Suzuki and Heck coupling reactions
    Hanhan, M. Emre
    [J]. APPLIED ORGANOMETALLIC CHEMISTRY, 2008, 22 (05) : 270 - 275
  • [50] Palladium-Catalyzed Oxidative Heck-Type Alkylation/Aryl Migration/Desulfonylation between Alkenes with α-Carbonyl Alkyl Bromides
    Fan, Jian-Hong
    Yang, Ji
    Song, Ren-Jie
    Li, Jin-Heng
    [J]. ORGANIC LETTERS, 2015, 17 (04) : 836 - 839
12345