Silver-Mediated Direct Amination of Benzoxazoles: Tuning the Amino Group Source from Formamides to Parent Amines

被引：273
|
作者：
Cho, Seung Hwan [1 ]
Kim, Ji Young [1 ]
Lee, S. Yunmi [1 ]
Chang, Sukbok [1 ]
机构：
[1] Korea Adv Inst Sci & Technol, Taejon 305701, South Korea
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2009年 / 48卷 / 48期
关键词：
amination; benzoxazoles; C-N coupling; formamides; silver; C-H BONDS; INTERMOLECULAR AMINATION; DIRECT ARYLATION; ARYL; FUNCTIONALIZATION; ALKENES; AMINOCARBONYLATION; HYDROAMINATION; AMIDATION; CLEAVAGE;
D O I：
10.1002/anie.200903957
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Formamides or parent amines were used as an amino group source for the silver-mediated amination of benzoxazoles. Although reactions with formamides proceeded at high temperatures, the direct amination with amines took place under much milder conditions (see scheme). Optically active amino groups could also be installed without racemization. © 2009 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码：9127 / 9130
页数：4
相关论文
共 5 条
  • [1] Copper-Catalyzed Direct Oxidative C-H Amination of Benzoxazoles with Formamides or Secondary Amines under Mild Conditions
    Li, Yaming
    Xie, Yusheng
    Zhang, Rong
    Jin, Kun
    Wang, Xiuna
    Duan, Chunying
    JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (13): : 5444 - 5449
  • [2] Silver-Mediated Trifluoromethylation of Aryldiazonium Salts: Conversion of Amino Group into Trifluoromethyl Group
    Wang, Xi
    Xu, Yan
    Mo, Fanyang
    Ji, Guojing
    Qiu, Di
    Feng, Jiajie
    Ye, Yuxuan
    Zhang, Songnan
    Zhang, Yan
    Wang, Jianbo
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (28) : 10330 - 10333
  • [3] Silver-mediated direct C-H amination of BODIPYs for screening endoplasmic reticulum-targeting reagents
    Zhang, Huaxing
    Chen, Xingyu
    Lan, Jingbo
    Liu, Yanhong
    Zhou, Fulin
    Wu, Di
    You, Jingsong
    CHEMICAL COMMUNICATIONS, 2018, 54 (26) : 3219 - 3222
  • [4] Direct use of formamides as amino group sources via C-N bond cleavage: a catalytic oxidative synthesis of α-ketoamides from acetophenones and formamides under metal-free conditions
    Zhao, Qiong
    Miao, Tao
    Zhang, Xiaobin
    Zhou, Wei
    Wang, Lei
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2013, 11 (11) : 1867 - 1873
  • [5] Electrochemically Mediated Synthesis of Cyanated Heterocycles from α-amino Esters, Pyridine-2-carbaldehydes and NH4SCN as Cyano Group Source
    Grishin, Sergei S.
    Ustyuzhanin, Alexander O.
    Vil', Vera A.
    Terent'ev., Alexander O.
    CHEMISTRY-A EUROPEAN JOURNAL, 2025,
1