Rhodium(III)-catalyzed internal oxidative coupling of N-hydroxyanilides with alkenes via C-H activation

被引：11
|
作者：
Wen, Jing [1 ]
Wu, An [2 ]
Chen, Pei [1 ]
Zhu, Jin [1 ]
机构：
[1] Nanjing Univ, Sch Chem & Chem Engn, State Key Lab Coordinat Chem, Nanjing Natl Lab Microstruct, Nanjing 210093, Jiangsu, Peoples R China
[2] Nanjing Univ, Kuang Yaming Honors Sch, Nanjing 210093, Jiangsu, Peoples R China
来源：
TETRAHEDRON LETTERS | 2015年 / 56卷 / 38期
基金：
中国国家自然科学基金;
关键词：
Rhodium; Anilides; Internal oxidation; Alkenes; C-H activation; BOND ACTIVATION; DIRECTING GROUP; ORTHO-ARYLATION; ANILIDES; INDOLES; ARENES; AMIDATION; ALKYNES; FUNCTIONALIZATION; CYCLIZATION;
D O I：
10.1016/j.tetlet.2015.07.070
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Described herein is an efficient new method for ortho-olefination of anilides in the presence of AgSbF6 and NaOAc via rhodium(III)-catalyzed internal oxidative C-H bond activation based on hydroxyl as directing and oxidative group. A range of alkenes and functional groups on acetanilides is supported and a possible mechanism is proposed according to the experimental results. (C) 2015 Elsevier Ltd. All rights reserved.
引用
收藏
页码：5282 / 5286
页数：5
相关论文
共 50 条
  • [1] Rh(III)-Catalyzed Oxidative Coupling of Unactivated Alkenes via C-H Activation
    Tsai, Andy S.
    Brasse, Mikael
    Bergman, Robert G.
    Ellman, Jonathan A.
    [J]. ORGANIC LETTERS, 2011, 13 (03) : 540 - 542
  • [2] Rhodium(iii)-catalyzed oxidative cross-coupling of benzoxazinones with styrenes via C-H activation
    Yang, Xifa
    Li, Song
    He, Yuhao
    Dai, Danhua
    Bao, Mengyao
    Luo, Ziyang
    Liu, Xiangyang
    Geng, Yuehua
    Fan, Liangxin
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2023, 21 (04) : 797 - 806
  • [3] Rhodium(III)-catalyzed oxidative annulation of N-arylbenzamidines with maleimides via dual C-H activation
    Sankaram, G. Siva
    Sahoo, Tanmoy
    Sridhar, B.
    Reddy, B. V. Subba
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2023, 21 (08) : 1719 - 1724
  • [4] Rh(III)-catalyzed oxidative coupling of unactivated alkenes via C-H activation: Reaction development and mechanistic insights
    Tsai, Andy S.
    Brasse, Mikael
    Ellman, Jonathan A.
    Bergman, Robert G.
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2012, 243
  • [5] Rhodium catalyzed C-H olefination of N-benzoylsulfonamides with internal alkenes
    Zhu, Chen
    Falck, John R.
    [J]. CHEMICAL COMMUNICATIONS, 2012, 48 (11) : 1674 - 1676
  • [6] Intermolecular coupling of isomerizable alkenes to heterocycles via rhodium-catalyzed C-H bond activation
    Tan, KL
    Bergman, RG
    Ellman, JA
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (47) : 13964 - 13965
  • [7] Rhodium-catalyzed coupling reactions of β- or α,β-substituted vinylpyridines with alkenes via C-H bond activation
    Lim, YG
    Kang, JB
    Lee, K
    Kim, YH
    [J]. HETEROATOM CHEMISTRY, 2002, 13 (04) : 346 - 350
  • [8] Rhodium(III)-Catalyzed Coupling of Arenes with Cyclopropanols via C-H Activation and Ring Opening
    Zhou, Xukai
    Yu, Songjie
    Kong, Lingheng
    Li, Xingwei
    [J]. ACS CATALYSIS, 2016, 6 (02): : 647 - 651
  • [9] Rhodium-catalyzed oxidative coupling of 2-aryl-imidazopyridines with internal alkynes via double C-H activation
    Kotla, Siva
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2015, 250
  • [10] Rhodium(III)-Catalyzed C-H Activation of Nitrones and Annulative Coupling with Nitroalkenes
    Bai, Dachang
    Jia, Qingqian
    Xu, Teng
    Zhang, Qiuqiu
    Wu, Fen
    Ma, Chaorui
    Liu, Bingxian
    Chang, Junbiao
    Li, Xingwei
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (18): : 9877 - 9884
12345