Thioethers as Directing Group for the Palladium-Catalyzed Direct Arylation of Arenes

被引:65
|
作者
Yao, Jinzhong [1 ]
Yu, Ming [1 ]
Zhang, Yuhong [1 ,2 ]
机构
[1] Zhejiang Univ, Dept Chem, Hangzhou 310027, Zhejiang, Peoples R China
[2] Lanzhou Univ, State Key Lab Appl Organ Chem, Lanzhou 730000, Peoples R China
关键词
arylation; C-H bond activation; palladium; potassium organotrifluoroborates; thioethers; C-H BONDS; CROSS-COUPLING REACTIONS; CARBON-HYDROGEN BONDS; ARYL CHLORIDES; BORONIC ACIDS; ARYLBORON REAGENTS; METAL-COMPLEXES; SUZUKI; ACTIVATION; HALIDES;
D O I
10.1002/adsc.201200447
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
Thioethers have proven to be efficient directing groups for the arylation of arenes under palladium catalysis. The thioether group can be readily removed or converted to other functional groups. Kinetic isotopic effect studies reveal that the C-H cleavage of arenes might be the turnover-limiting step.
引用
收藏
页码:3205 / 3210
页数:6
相关论文
共 50 条
  • [31] Palladium-catalyzed direct arylation of indoles with arylsulfonyl hydrazides
    Liu, Congrong
    Ding, Lianghui
    Guo, Guang
    Liu, Weiwei
    Yang, Fu-Lai
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2016, 14 (10) : 2824 - 2827
  • [32] Intramolecular palladium-catalyzed direct arylation of alkenyl triflates
    Cruz, Ana C. F.
    Miller, Neil D.
    Willis, Michael C.
    ORGANIC LETTERS, 2007, 9 (21) : 4391 - 4393
  • [33] Palladium-catalyzed redox cascade for direct β-arylation of ketones
    Huang, Zhongxing
    Dong, Guangbin
    TETRAHEDRON, 2018, 74 (26) : 3253 - 3265
  • [34] Development of Palladium-Catalyzed Direct Arylation Polymerization (DArP)
    Wakioka, Masayuki
    Ozawa, Fumiyuki
    JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 2017, 75 (08) : 810 - 820
  • [35] Palladium-catalyzed electrophilic C-H fluorination of arenes using oxazoline as a removable directing group
    Gutierrez, David A.
    Lee, Wan-Chen Cindy
    Shen, Yuning
    Li, Jie Jack
    TETRAHEDRON LETTERS, 2016, 57 (48) : 5372 - 5376
  • [36] Palladium-Catalyzed Direct Arylation of Heteroarenes with Aryl Mesylates
    So, Chau Ming
    Lau, Chak Po
    Kwong, Fuk Yee
    CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (03) : 761 - 765
  • [37] Palladium-Catalyzed C(sp2)-H Arylation Using Formamide as a Transformable Directing Group
    Wan, Congqing
    Zhao, Jiaji
    Xu, Mingfang
    Huang, Jinbo
    JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (10): : 4751 - 4756
  • [38] Double C-H Activation: The Palladium-Catalyzed Direct C-Arylation of Xanthines with Arenes
    Malakar, Chandi C.
    Schmidt, Dietmar
    Conrad, Juergen
    Beifuss, Uwe
    ORGANIC LETTERS, 2011, 13 (06) : 1378 - 1381
  • [39] Palladium-Catalyzed γ-C(sp3)-H Arylation of Thiols by a Detachable Protecting/Directing Group
    Jin, Likun
    Wang, Jianchun
    Dong, Guangbin
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (38) : 12352 - 12355
  • [40] Palladium-catalyzed α-arylation of sulfoximines
    Cho, GY
    Bolm, C
    ORGANIC LETTERS, 2005, 7 (07) : 1351 - 1354