Palladium-Catalyzed Direct C-H Arylation of Enamides with Simple Arenes

被引:150
|
作者
Pankajakshan, Sreekumar [2 ]
Xu, Yun-He [1 ]
Cheng, Jun Kee [2 ]
Low, Man Ting [2 ]
Loh, Teck-Peng [1 ,2 ]
机构
[1] Univ Sci & Technol China, Dept Chem, Hefei 230026, Peoples R China
[2] Nanyang Technol Univ, Sch Phys & Math Sci, Div Chem & Biol Chem, Singapore 637371, Singapore
关键词
arylation; C-H functionalization; enamides; palladium; synthetic methods; ELECTRON-RICH OLEFINS; REGIOSELECTIVE HECK ARYLATION; ACYL-N-VINYLAMINE; STEREOSELECTIVE-SYNTHESIS; BOND ACTIVATION; FUNCTIONALIZATION; CARBOXYLATION; ALKENYLATION; REACTIVITY; INDOLES;
D O I
10.1002/anie.201109247
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Z only: An atom-economical synthetic route towards arylated Z-enamides through double C-H functionalization is described. The Z/E selectivity of the palladium-catalyzed monoarylation is absolute (step A in scheme), and the molecular complexity of the products can be further endowed by a sequential second arylation, which requires the use of trifluoracetic acid (TFA; step B). Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码:5701 / 5705
页数:5
相关论文
共 50 条
  • [41] Directed Palladium-Catalyzed Oxidative C-H Arylation of (Hetero)arenes with Arylboronic Acids by Using TEMPO
    Kirchberg, Sylvia
    Vogler, Thomas
    Studer, Armido
    SYNLETT, 2008, (18) : 2841 - 2845
  • [42] Palladium-Catalyzed C-H Acylation of Arenes Using Thioethers as Directing Groups
    Xu, Bo
    Liu, Wei
    Kuang, Chunxiang
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 2014 (12) : 2576 - 2583
  • [43] Palladium-Catalyzed Oxidative Arylation of 1H-Indazoles with Arenes
    Gambouz, Khadija
    El Abbouchi, Abdelmoula
    Nassiri, Sarah
    Suzenet, Franck
    Bousmina, Mostapha
    Akssira, Mohamed
    Guillaumet, Gerald
    El Kazzouli, Said
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 2020 (48) : 7435 - 7439
  • [44] Palladium-catalyzed oxime ether directed regioselective C-H alkoxylation of arenes
    Pan, Liang
    Wang, Liang
    Chen, Qun
    He, Mingyang
    SYNTHETIC COMMUNICATIONS, 2016, 46 (24) : 1981 - 1988
  • [45] Palladium-Catalyzed Direct Alkynylation of C-H Bonds in Benzenes
    Tobisu, Mamoru
    Ano, Yusuke
    Chatani, Naoto
    ORGANIC LETTERS, 2009, 11 (15) : 3250 - 3252
  • [46] Intramolecular Palladium-Catalyzed Alkane C-H Arylation from Aryl Chlorides
    Rousseaux, Sophie
    Davi, Michael
    Sofack-Kreutzer, Julien
    Pierre, Cathleen
    Kefalidis, Christos E.
    Clot, Eric
    Fagnou, Keith
    Baudoin, Olivier
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (31) : 10706 - 10716
  • [47] Palladium-catalyzed carbonylative C-H activation of arenes with norbornene as the coupling partner
    Chen, Jianbin
    Natte, Kishore
    Wu, Xiao-Feng
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2016, 803 : 9 - 12
  • [48] Palladium-Catalyzed ortho-Selective C-H Chlorination of Arenes Using Anodic Oxidation
    Yang Qi-Liang
    Wang Xiang-Yang
    Weng Xin-Jun
    Yang Xiang
    Xu Xue-Tao
    Tong Xiaofeng
    Fang Ping
    Wu Xin-Yan
    Mei Tian-Sheng
    ACTA CHIMICA SINICA, 2019, 77 (09) : 866 - 873
  • [49] Palladium-Catalyzed C-H Iodination of Arenes by Means of Sulfinyl Directing Groups
    Saito, Hayate
    Yamamoto, Keita
    Sumiya, Yosuke
    Liu, Ling-Jun
    Nogi, Keisuke
    Maeda, Satoshi
    Yorimitsu, Hideki
    CHEMISTRY-AN ASIAN JOURNAL, 2020, 15 (16) : 2442 - 2446
  • [50] Highly Regioselective α-Arylation of Coumarins via Palladium-Catalyzed C-H Activation/Desulfitative Coupling
    Jafarpour, Farnaz
    Olia, Mina Barzegar Amiri
    Hazrati, Hamideh
    ADVANCED SYNTHESIS & CATALYSIS, 2013, 355 (17) : 3407 - 3412