Palladium-Catalyzed Cross-Coupling of Aryl Chlorides and Tosylates with Hydrazine

被引:140
|
作者
Lundgren, Rylan J. [1 ]
Stradiotto, Mark [1 ]
机构
[1] Dalhousie Univ, Dept Chem, Halifax, NS B3H 4J3, Canada
基金
加拿大自然科学与工程研究理事会;
关键词
amination; cross-coupling; homogeneous catalysis; hydrazine; P; N ligands; N-ARYLATION; C-N; EFFICIENT SYNTHESIS; INTRAMOLECULAR AMINATION; REGIOSELECTIVE SYNTHESIS; HALIDES; 1-ARYL-1H-INDAZOLES; AMMONIA; N; N-DIALKYLHYDRAZINES; CONVERSION;
D O I
10.1002/anie.201003764
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Hydrazine is not a problem anymore: The title transformation is the first reaction to yield aryl hydrazines through the cross-coupling of aryl chlorides and tosylates with hydrazine. An appropriately designed palladium catalyst allows this reaction to proceed rapidly under mild conditions, and with excellent chemoselectivity (see scheme; Ad=adamantyl, Ts=4-toluenesulfonyl). © 2010 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码:8686 / 8690
页数:5
相关论文
共 50 条
  • [1] Palladium-catalyzed cross-coupling reaction of silicone with aryl chlorides
    Koike, T
    Mori, A
    SYNLETT, 2003, (12) : 1850 - 1852
  • [2] Palladium-Catalyzed Hiyama Cross-Coupling of Aryltrifluorosilanes with Aryl and Heteroaryl Chlorides
    Molander, Gary A.
    Iannazzo, Laura
    JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (21) : 9182 - 9187
  • [3] Ligand-supported palladium-catalyzed cross-coupling reactions of (hetero) aryl chlorides
    Onoabedje, Efeturi Abraham
    Okoro, Uchechukwu Chris
    SYNTHETIC COMMUNICATIONS, 2019, 49 (17) : 2117 - 2146
  • [4] Palladium-catalyzed cross-coupling reactions of aryl mesylates
    So, Chau Ming
    Kwong, Fuk Yee
    CHEMICAL SOCIETY REVIEWS, 2011, 40 (10) : 4963 - 4972
  • [5] Palladium-catalyzed carbonylative transformation of aryl chlorides and aryl tosylates
    Wu, Xiao-Feng
    RSC ADVANCES, 2016, 6 (87): : 83831 - 83837
  • [6] Palladium-catalyzed cross-coupling reaction of organobismuth compounds with aryl and alkenyl chlorides
    Yamazaki, O
    Tanaka, T
    Shimada, S
    Suzuki, Y
    Tanaka, M
    SYNLETT, 2004, (11) : 1921 - 1924
  • [7] Additive-Free Palladium-Catalyzed Decarboxylative Cross-Coupling of Aryl Chlorides
    Daley, Ryan A.
    Liu, En-Chih
    Topczewski, Joseph J.
    ORGANIC LETTERS, 2019, 21 (12) : 4734 - 4738
  • [8] Nickel-Catalyzed Cross-Coupling of Sulfonamides With (Hetero)aryl Chlorides
    McGuire, Ryan T.
    Simon, Connor M.
    Yadav, Arun A.
    Ferguson, Michael J.
    Stradiotto, Mark
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (23) : 8952 - 8956
  • [9] Palladium-Catalyzed Monoarylation of Aryl Amine with Aryl Tosylates
    Xie, Xiaomin
    Ni, Gang
    Ma, Fangfang
    Ding, Lina
    Xu, Sheng
    Zhang, Zhaoguo
    SYNLETT, 2011, (07) : 955 - 958
  • [10] Palladium-Catalyzed Cross-Coupling of Aryl Bromides and Chlorides with Trimethylsilylalkynes under Mild Conditions
    Tlahuext-Aca, Adrian
    Nguyen, Quyen D.
    Gao, Yang
    Sati, Girish C.
    Zhao, Jinpeng
    Valco, Daniel
    JOURNAL OF ORGANIC CHEMISTRY, 2024, 89 (18) : 13762 - 13767