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
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2010年 / 49卷 / 46期
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
  • [31] Palladium-Catalyzed Cross-Coupling of Aryl Halides Using Organotitanium Nucleophiles
    Lee, Hang Wai
    Lam, Fuk Loi
    So, Chau Ming
    Lau, Chak Po
    Chan, Albert S. C.
    Kwong, Fuk Yee
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (40) : 7436 - 7439
  • [32] Palladium-catalyzed cross-coupling of benzyltitanium(IV) reagents with aryl fluorides
    Li, Yan
    MONATSHEFTE FUR CHEMIE, 2022, 153 (02): : 193 - 199
  • [33] Palladium-catalyzed cross-coupling reaction of potassium diaryldifluoroborates with aryl halides
    Ito, T
    Iwai, T
    Mizuno, T
    Ishino, Y
    SYNLETT, 2003, (10) : 1435 - 1438
  • [34] Palladium-catalyzed cross-coupling reaction of aryl trimethoxysilanes with terminal alkynes
    Ye, Zhishi
    Liu, Miaochang
    Lin, Baoda
    Wu, Huayue
    Ding, Jinchang
    Cheng, Jiang
    TETRAHEDRON LETTERS, 2009, 50 (05) : 530 - 532
  • [35] Palladium-Catalyzed Direct Cross-Coupling of Carboranyllithium with (Hetero)Aryl Halides
    Lu, Ju-You
    Wan, Hong
    Zhang, Jianwei
    Wang, Zhixuan
    Li, Yang
    Du, Yongmei
    Li, Chunying
    Liu, Zhao-Tie
    Liu, Zhong-Wen
    Lu, Jian
    CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (49) : 17542 - 17546
  • [36] Palladium-Catalyzed Desulfitative Cross-Coupling of Sodium Arylsulfinates with Aryl Bromides and Chlorides: An Alternative Convenient Synthesis of Biaryls
    Zhou, Chao
    Li, Yaming
    Lu, Yang
    Zhang, Rong
    Jin, Kun
    Fu, Xinmei
    Duan, Chunying
    CHINESE JOURNAL OF CHEMISTRY, 2013, 31 (10) : 1269 - 1273
  • [37] Palladium-catalyzed cross-coupling of aroyl chlorides with aryl stannanes in the presence of triethylsilane: Efficient access to aromatic ketones
    Higashi, Shoko
    Uno, Sota
    Ohsuga, Yui
    Noumi, Maiko
    Saito, Ryota
    TETRAHEDRON LETTERS, 2020, 61 (45)
  • [38] A Ligand-Free Palladium-Catalyzed Cross-Coupling of Aryl Sulfinates with Aryl Bromides
    Ortgies, Dirk H.
    Forgione, Pat
    SYNLETT, 2013, 24 (13) : 1715 - 1721
  • [39] Palladium-Catalyzed Cross-Coupling Reaction of AlArEt2(THF) with Aryl Bromides
    Shu, Wan-Ting
    Zhou, Shuangliu
    Gau, Han-Mou
    SYNTHESIS-STUTTGART, 2009, (23): : 4075 - 4081
  • [40] A P,N-Ligand for Palladium-Catalyzed Ammonia Arylation: Coupling of Deactivated Aryl Chlorides, Chemoselective Arylations, and Room Temperature Reactions
    Lundgren, Rylan J.
    Peters, Brendan D.
    Alsabeh, Pamela G.
    Stradiotto, Mark
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (24) : 4071 - 4074
12345