Classical Reagents: New Surprises in Palladium-Catalyzed C-C Coupling Reactions

被引:30
|
作者
Lindhardt, Anders T. [1 ,2 ]
Skrydstrup, Troels [1 ,2 ]
机构
[1] Aarhus Univ, Dept Chem, Ctr Insoluble Prot Struct inSPIN, DK-8000 Aarhus, Denmark
[2] Aarhus Univ, Interdisciplinary Nanosci Ctr, DK-8000 Aarhus, Denmark
基金
新加坡国家研究基金会;
关键词
alkynes; hydride elimination; C-C coupling reactions; hydropalladation; palladium;
D O I
10.1002/chem.200800608
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
From investigations on a relatively simple concept to identify conditions for promoting Mizoroki-Heck reactions with vinyl tosylates and phosphates, two serendipitous discoveries were made concerning new properties of palladium as a catalyst. In the first case, beta-hydride eliminations well known for alkyl metal complexes were found to be equally feasible with alkenyl metal compounds. And secondly, conditions were found for promoting intermolecular ene-yne couplings via a Pd-II-H intermediate. This coupling reactions represents an atom economical Mizoroki-Heck type reaction.
引用
收藏
页码:8756 / 8766
页数:11
相关论文
共 50 条
  • [21] Fused Indolines by Palladium-Catalyzed Asymmetric C-C Coupling Involving an Unactivated Methylene Group
    Nakanishi, Masafumi
    Katayev, Dmitry
    Besnard, Celine
    Kuendig, E. Peter
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (32) : 7438 - 7441
  • [22] Palladium-catalyzed dehydroarylation of triarylmethanols and their coupling with unsaturated compounds accompanied by C-C bond cleavage
    Terao, Y
    Nomoto, M
    Satoh, T
    Miura, M
    Nomura, M
    JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (20): : 6942 - 6944
  • [23] Orthometallated palladium trimers in C-C coupling reactions
    Baszczyk, Izabela
    Gniewek, Andrzej
    Trzeciak, Anna M.
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2012, 710 : 44 - 52
  • [24] C,C-Diacetylenic phosphaalkenes in palladium-catalyzed cross-coupling reactions
    Oberg, Elisabet
    Geng, Xue-Li
    Santoni, Marie-Pierre
    Ott, Sascha
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2011, 9 (18) : 6246 - 6255
  • [25] Palladium-catalyzed C-N Coupling Reactions in the Synthesis of Dibenzodiazepines
    Grewal, Pooja
    Kaur, Navjeet
    CURRENT ORGANIC CHEMISTRY, 2022, 26 (20) : 1813 - 1826
  • [26] Hetaryl Bromides Bearing the SO2F Group - Versatile Substrates for Palladium-Catalyzed C-C Coupling Reactions
    Cherepakha, Artem Yu.
    Stepannikova, Kateryna O.
    Vashchenko, Bohdan V.
    Gorichko, Marian V.
    Tolmachev, Andrey A.
    Grygorenko, Oleksandr O.
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 2018 (47) : 6682 - 6692
  • [27] Expedient Synthesis of Terminal Vinylphosphonates by Palladium-Catalyzed C-C Cross-Coupling Reactions of (1-Halovinyl)phosphonates
    Fang, Yewen
    Zhang, Li
    Jin, Xiaoping
    Li, Jinjian
    Yuan, Meijuan
    Li, Ruifeng
    Gao, Haoqi
    Fang, Jianghua
    Liu, Yuyan
    SYNLETT, 2015, 26 (07) : 980 - 984
  • [28] New Progress in C-C Coupling Reactions Catalyzed by Supported N-Heterocyclic Carbene Palladium Complex
    Yuan, Dingzhong
    Zhang, Qinghua
    Liao, Shijun
    Xiong, Wenwen
    Yuan, Ligang
    Cai, Qisheng
    Yang, Mengmei
    Li, Xiong
    Jiang, Yejia
    Liu, Yan
    Li, Ping
    Xu, Zhenshuai
    Sun, Panpan
    Geng, Huiling
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2015, 35 (05) : 961 - 974
  • [29] New palladium catalyst for C-C coupling reactions in ionic liquids.
    Welton, T
    Smith, PJ
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2002, 224 : U629 - U629
  • [30] Synthesis of benzannulated N-heterocycles by a palladium-catalyzed C-C/C-N coupling of bromoalkylamines
    Thansandote, Praew
    Raemy, Manuel
    Rudolph, Alena
    Lautens, Mark
    ORGANIC LETTERS, 2007, 9 (25) : 5255 - 5258