Cu/Pd cooperatively catalyzed tandem intramolecular anti-Markovnikov hydroarylation of unsaturated amides: facile construction of 3,4-dihydroquinolinones via borylation/intramolecular C(sp3)-C(sp2) cross coupling

被引：38
作者：
Kuang, Zhijie [1 ]
Li, Bingnan [1 ]
Song, Qiuling [1 ]
机构：
[1] Huaqiao Univ, Coll Mat Sci Engn, Coll Chem Engn, Inst Next Generat Matter Transformat, Xiamen 361021, Fujian, Peoples R China
来源：
CHEMICAL COMMUNICATIONS | 2018年 / 54卷 / 01期
关键词：
PALLADIUM/COPPER CATALYSIS; SYNERGISTIC CATALYSIS; EFFICIENT ROUTE; BORONIC ESTERS; H BOND; ALKENES; CARBOBORATION; ARYLBORATION; CYCLIZATION; ALKYNES;
D O I：
10.1039/c7cc07180a
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
An anti-Markovnikov hydroarylation of unsaturated amides via a Cu/Pd synergistically catalyzed cascade borylation/intramolecular sp(2)-sp(3) cross-coupling has been disclosed. 3,4-Dihydroquinolinones, one type of important scaffold prevailing in pharmaceuticals and biologically active compounds, could be readily accessible with high regio-selectivity and high yields.
引用
收藏
页码：34 / 37
页数：4
相关论文
共 33 条
  • [1] AUTOXIDATION IN BASIC MEDIA .4. HYDROCARBON AUTOXIDATION
    BARTON, DHR
    JONES, DW
    [J]. JOURNAL OF THE CHEMICAL SOCIETY, 1965, (JUN): : 3563 - &
  • [2] Synthesis of multi-labeled [14C]Aripiprazole
    Bonacorsi, SJ
    Waller, SC
    Rinehart, JK
    [J]. JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS, 2006, 49 (01) : 1 - 9
  • [3] Enantioselective Copper(I)-Catalyzed Borylative Aldol Cyclizations of Enone Diones
    Burns, Alan R.
    Gonzalez, Jorge Solana
    Lam, Hon Wai
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (43) : 10827 - 10831
  • [4] Development and Kilogram-Scale Synthesis of a D2/5-HT2A Receptor Dual Antagonist (±)-SIPI 6360
    Chen, Xiao-Wen
    Liu, Yu
    Jin, Xun-Qi
    Sun, Yuan-Yuan
    Gu, Shun-Lin
    Fu, Lei
    Li, Jian-Qi
    [J]. ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2016, 20 (09) : 1662 - 1667
  • [5] Asymmetric Hydroarylation of Vinylarenes Using a Synergistic Combination of CuH and Pd Catalysis
    Friis, Stig D.
    Pirnot, Michael T.
    Buchwald, Stephen L.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (27) : 8372 - 8375
  • [6] Palladium-catalyzed reductive coupling of styrenes and organostannanes under aerobic conditions
    Gligorich, Keith M.
    Cummings, Sarah A.
    Sigman, Matthew S.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (46) : 14193 - +
  • [7] Selective Dual Inhibitors of CYP19 and CYP11B2: Targeting Cardiovascular Diseases Hiding in the Shadow of Breast Cancer
    Hu, Qingzhong
    Yin, Lina
    Hartmann, Rolf W.
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 2012, 55 (16) : 7080 - 7089
  • [8] A Cu/Pd Cooperative Catalysis for Enantioselective Allylboration of Alkenes
    Jia, Tao
    Cao, Peng
    Wang, Bing
    Lou, Yazhou
    Yin, Xuemei
    Wang, Min
    Liao, Jian
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (43) : 13760 - 13763
  • [9] Koreeda M., 1984, J ORG CHEM, V49, P2081
  • [10] Versatile Relay and Cooperative Palladium(0) N-Heterocyclic Carbene/Copper(I) N-Heterocyclic Carbene Catalysis for the Synthesis of Tri- and Tetrasubstituted Alkenes
    Lesieur, Mathieu
    Bidal, Yannick D.
    Lazreg, Faima
    Nahra, Fady
    Cazin, Catherine S. J.
    [J]. CHEMCATCHEM, 2015, 7 (14) : 2108 - 2112
1234