Copper-Catalyzed Borylacylation of Activated Alkenes with Acid Chlorides

被引:102
|
作者
Huang, Yuan [1 ]
Smith, Kevin B. [1 ]
Brown, M. Kevin [1 ]
机构
[1] Indiana Univ, Dept Chem, 800 E Kirkwood Ave, Bloomington, IN 47401 USA
基金
美国国家卫生研究院;
关键词
acid chlorides; alkenes; boron; copper; homogeneous catalysis; KETONE SYNTHESIS; ENANTIOSELECTIVE ARYLBORATION; ACYL CHLORIDES; CARBOBORATION; DERIVATIVES; BORYLATION; ALDEHYDES; REAGENTS; ALLENES; ESTERS;
D O I
10.1002/anie.201707323
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A method for the copper-catalyzed borylacylation of activated alkenes is presented. The reaction involves borylcupration of the alkene, followed by capture of the generated alkyl-copper intermediate with an acid chloride. The reactions operated with low catalyst loading and generally occurre within 15min at room temperature for a range of activated alkenes. In the case of vinyl arenes, enantioselective borylacylation was possible.
引用
收藏
页码:13314 / 13318
页数:5
相关论文
共 50 条
  • [21] Copper-Catalyzed Radical Aminotrifluoromethylation of Alkenes
    Xiao, Haiwen
    Shen, Haigen
    Zhu, Lin
    Li, Chaozhong
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2019, 141 (29) : 11440 - 11445
  • [22] Copper-catalyzed intermolecular aminochlorination of alkenes
    Arteaga, Gean C.
    Saavedra-Olavarria, Jorge
    Almendras, Sebastian
    Hermosilla-Ibanez, Patricio
    Almodovar, Iriux
    Perez, Edwin G.
    TETRAHEDRON LETTERS, 2018, 59 (12) : 1091 - 1093
  • [23] Copper-catalyzed trifluoromethylation of alkenes and alkynes
    Janson, Par G.
    Ilchenko, Nadia O.
    Ghoneim, Ibrahim
    Szabo, Kalman J.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2013, 245
  • [24] Copper-catalyzed cycloaddition between hydrogen phosphonates and activated alkenes: synthesis of phosphonoisoquinolinediones
    Wu, Ju
    Gao, Yuzhen
    Zhao, Xin
    Zhang, Liangliang
    Chen, Weizhu
    Tang, Guo
    Zhao, Yufen
    RSC ADVANCES, 2016, 6 (01) : 303 - 306
  • [25] PALLADIUM-CATALYZED ACYLATION OF ACTIVATED ALKENES WITH BRIDGEHEAD ACID-CHLORIDES
    HORI, K
    ANDO, M
    TAKAISHI, N
    INAMOTO, Y
    TETRAHEDRON LETTERS, 1987, 28 (47) : 5883 - 5886
  • [26] Insight into the Copper-Catalyzed Borylation of Strained Alkenes
    Parra, Alejandro
    Lopez, Aurora
    Diaz-Tendero, Sergio
    Amenos, Laura
    Garcia Ruano, Jose Luis
    Tortosa, Mariola
    SYNLETT, 2015, 26 (04) : 494 - 500
  • [27] Copper-Catalyzed Bromodifluoroacetylation of Alkenes with Ethyl Bromodifluoroacetate
    Li, Dengke
    Mao, Tingting
    Huang, Jinbo
    Zhu, Qiang
    JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (17): : 10445 - 10452
  • [28] Copper-Catalyzed Vicinal Thiocyanosulfonylation of Alkenes and Alkynes
    Duan, Meng-Fan
    Xiao, Mei
    Ogundipe, Olukayode Olamiji
    Wu, Xin-Xin
    Zou, Jian-Ping
    JOURNAL OF ORGANIC CHEMISTRY, 2024, 89 (16): : 11558 - 11566
  • [29] Enantioselective Copper-Catalyzed Carboetherification of Unactivated Alkenes
    Bovino, Michael T.
    Liwosz, Timothy W.
    Kendel, Nicole E.
    Miller, Yan
    Tyminska, Nina
    Zurek, Eva
    Chemler, Sherry R.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (25) : 6383 - 6387
  • [30] Copper-Catalyzed Enantioselective Radical Chlorination of Alkenes
    Wu, Dunqi
    Fan, Wenzheng
    Wu, Lianqian
    Chen, Pinhong
    Liu, Guosheng
    ACS CATALYSIS, 2022, 12 (09) : 5284 - 5291