Rhodium-catalyzed Electrophilic Amination of Arylboronic Acids with Secondary Hydroxylamines

被引:13
|
作者
Yasuhisa, Tomohiro [1 ]
Hirano, Koji [1 ]
Miura, Masahiro [1 ]
机构
[1] Osaka Univ, Grad Sch Engn, Dept Appl Chem, Suita, Osaka 5650871, Japan
关键词
Arylamine; Electrophilic amination; Rhodium catalyst; HETEROARENES; AMIDATION; ALKYL;
D O I
10.1246/cl.161158
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A rhodium(III)-catalyzed electrophilic amination of arylboronic acids with secondary hydroxylamines has been developed. The rhodium catalysis is compatible with heteroarylboronic acids as well as acyl and alkoxycarbonyl protecting groups on the nitrogen of O-acylhydroxylamines, and the corresponding secondary anilines are obtained in good to excellent yields.
引用
收藏
页码:463 / 465
页数:3
相关论文
共 50 条
  • [21] Stereoselective Rhodium-Catalyzed Amination of Alkenes
    Lebel, Helene
    Spitz, Cedric
    Leogane, Olivier
    Trudel, Carl
    Parmentier, Michael
    ORGANIC LETTERS, 2011, 13 (20) : 5460 - 5463
  • [22] Stereoselective synthesis of α-allenols by rhodium-catalyzed reaction of alkynyl oxiranes with arylboronic acids
    Miura, Tomoya
    Shimada, Masahiko
    Ku, Sung-Yu
    Tamai, Tomohiro
    Murakami, Masahiro
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (37) : 7101 - 7103
  • [23] Density functional theory insights into rhodium-catalyzed addition of arylboronic acids to ketones
    Miro, Pere
    Recio, Rocio
    Fernandez, Inmaculada
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2018, 255
  • [24] A simple rhodium-catalyzed addition reaction of aldehydes with arylboronic acids in aqueous ?-valerolactone
    Xu, Min-xiao
    Zhang, Kai-ming
    Zhang, Jie
    MENDELEEV COMMUNICATIONS, 2022, 32 (03) : 397 - 398
  • [25] Rhodium-catalyzed addition/ring-opening reaction of arylboronic acids with cyclobutanones
    Matsuda, T
    Makino, M
    Murakami, M
    ORGANIC LETTERS, 2004, 6 (08) : 1257 - 1259
  • [26] Novel hexadentate imidazolium salts in the rhodium-catalyzed addition of arylboronic acids to aldehydes
    Chen, JH
    Zhang, XQ
    Feng, Q
    Luo, MM
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2006, 691 (03) : 470 - 474
  • [27] Rhodium-Catalyzed Asymmetric Addition of Arylboronic Acids to β-Phthaliminoacrylate Esters toward the Synthesis of β-Amino Acids
    Nishimura, Takahiro
    Wang, Jun
    Nagaosa, Makoto
    Okamoto, Kazuhiro
    Shintani, Ryo
    Kwong, Fuk-yee
    Yu, Wing-yiu
    Chan, Albert S. C.
    Hayashi, Tamio
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (02) : 464 - +
  • [28] Cp*Rh(III)-catalyzed electrophilic amination of arylboronic acids with azo compounds for synthesis of arylhydrazides
    Lau, Yan-Fung
    Chan, Chun-Ming
    Zhou, Zhongyuan
    Yu, Wing-Yiu
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2016, 14 (28) : 6821 - 6825
  • [29] Rhodium-Catalyzed Regioselective Amination of Secondary Allylic Trichloroacetimidates with Unactivated Aromatic Amines
    Arnold, Jeffrey S.
    Stone, Robert F.
    Nguyen, Hien M.
    ORGANIC LETTERS, 2010, 12 (20) : 4580 - 4583
  • [30] Rhodium-Catalyzed Asymmetric Amination of Allylic Trichloroacetimidates
    Arnold, Jeffrey S.
    Nguyen, Hien M.
    SYNTHESIS-STUTTGART, 2013, 45 (15): : 2101 - 2108