Palladium-Catalyzed Sequential Formation of C-C Bonds: Efficient Assembly of 2-Substituted and 2,3-Disubstituted Quinolines

被引:100
作者
Ji, Xiaochen [1 ]
Huang, Huawen [1 ]
Li, Yibiao [1 ]
Chen, Huoji [1 ]
Jiang, Huanfeng [1 ]
机构
[1] S China Univ Technol, Sch Chem & Chem Engn, Guangzhou 510640, Guangdong, Peoples R China
基金
中国国家自然科学基金;
关键词
C?C bond formation; oxidation; palladium; quinolines; 3-COMPONENT POVAROV REACTION; ARENE CARBOXYLIC-ACIDS; SUBSTITUTED QUINOLINES; DECARBOXYLATIVE OLEFINATION; HETEROAROMATIC-COMPOUNDS; BIOLOGICAL EVALUATION; ANTIBACTERIAL AGENTS; MOLECULAR-OXYGEN; DIRECT ARYLATION; AROMATIC-AMINES;
D O I
10.1002/anie.201202412
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A series of substituted quinolines was prepared from arylamines, aldehydes, and terminal olefins (see scheme). The palladium-catalyzed sequential formation of C-C bonds proceeds smoothly with both electron-deficient and electron-rich olefins. When acrylic acid is used as terminal olefin, decarboxylation occurs to provide 2-substituted quinolines. Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码:7292 / 7296
页数:5
相关论文
共 80 条
  • [51] Cooperative Catalysis with Metal and Secondary Amine: Synthesis of 2-Substituted Quinolines via Addition/Cycloisomerization Cascade
    Patil, Nitm T.
    Raut, Vivek S.
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (20) : 6961 - 6964
  • [52] Povarov L.S., 1967, RUSS CHEM REV+, V36, P656, DOI [10.1070/RC1967v036n09ABEH001680, DOI 10.1070/RC1967V036N09ABEH001680]
  • [53] Recent advances in transition metal catalyzed oxidation of organic substrates with molecular oxygen
    Punniyamurthy, T
    Velusamy, S
    Iqbal, J
    [J]. CHEMICAL REVIEWS, 2005, 105 (06) : 2329 - 2363
  • [54] A CONVENIENT SYNTHESIS OF SUBSTITUTED QUINOLINES BY THERMAL ELECTROCYCLIC REARRANGEMENT OF ORTHO-VINYL ANILS UNDER NONACIDIC CONDITIONS
    QIANG, LG
    BAINE, NH
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (18) : 4218 - 4222
  • [55] TEMPO Oxoammonium Salt-Mediated Dehydrogenative Povarov/Oxidation Tandem Reaction of N-Alkyl Anilines
    Richter, Heinrich
    Mancheno, Olga Garcia
    [J]. ORGANIC LETTERS, 2011, 13 (22) : 6066 - 6069
  • [56] From Sensors to Silencers: Quinoline-and Benzimidazole-Sulfonamides as Inhibitors for Zinc Proteases
    Rouffet, Matthieu
    de Oliveira, Cesar Augusto F.
    Udi, Yael
    Agrawal, Arpita
    Sagi, Irit
    McCammon, J. Andrew
    Cohen, Seth M.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (24) : 8232 - +
  • [57] Direct transition metal-catalyzed functionalization of heteroaromatic compounds
    Seregin, Ilya V.
    Gevorgyan, Vladimir
    [J]. CHEMICAL SOCIETY REVIEWS, 2007, 36 (07) : 1173 - 1193
  • [58] A Facile Synthesis of Substituted 2-Alkylquinolines through [3+3] Annulation between 3-Ethoxycyclobutanones and Aromatic Amines at Room Temperature
    Shan, Gang
    Sun, Xiuyun
    Xia, Qian
    Rao, Yu
    [J]. ORGANIC LETTERS, 2011, 13 (21) : 5770 - 5773
  • [59] Hafnium (IV) Bis(perfluorooctanesulfonyl)amide-Catalyzed One-Pot Synthesis of Substituted Quinolines in Fluorous Media
    Shen, Ming-Gui
    Cai, Chun
    Yi, Wen-Bin
    [J]. JOURNAL OF HETEROCYCLIC CHEMISTRY, 2009, 46 (04) : 796 - 799
  • [60] Recent advances in transition-metal catalyzed reactions using molecular oxygen as the oxidant
    Shi, Zhuangzhi
    Zhang, Chun
    Tang, Conghui
    Jiao, Ning
    [J]. CHEMICAL SOCIETY REVIEWS, 2012, 41 (08) : 3381 - 3430