Inverted regioselectivity of C-H amination: Unexpected oxidation at β- rather than γ-C-H

被引：12
|
作者：
Wyszynski, Filip J. [1 ]
Thompson, Amber L. [1 ]
Davis, Benjamin G. [1 ]
机构：
[1] Univ Oxford, Dept Chem, Chem Res Lab, 12 Mansfield Rd, Oxford OX1 3TA, England
来源：
ORGANIC & BIOMOLECULAR CHEMISTRY | 2010年 / 8卷 / 19期
基金：
英国工程与自然科学研究理事会; 英国生物技术与生命科学研究理事会;
关键词：
RH-CATALYZED AMINATION; INTRAMOLECULAR AMIDATION; ABSOLUTE-STRUCTURE; BONDS; FUNCTIONALIZATION; DERIVATIVES; CONVERSION; MECHANISM;
D O I：
10.1039/c0ob00113a
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A rare example of beta- over gamma-C-H selectivity during Rh-catalysed sulfamate ester cyclisation is presented; from derivatives of 1,6-anhydro-beta-D-mannopyranose, five-membered sulfamidates were formed in preference to the typical six-membered oxathiazinane intramolecular insertion products. A 3D structure of sulfamate 1 helps to rationalise this unusual selectivity and analyses suggest that n ->sigma*(CH) interactions may be a key controlling factor.
引用
收藏
页码：4246 / 4248
页数：3
相关论文
共 50 条
  • [31] Electrophotocatalytic C-H Functionalization of Ethers with High Regioselectivity
    Huang, He
    Strater, Zack M.
    Lambert, Tristan H.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2020, 142 (04) : 1698 - 1703
  • [32] Supported Single Atom Catalysts for C-H Activation: Selective C-H Oxidations, Dehydrogenations and Oxidative C-H/C-H Couplings
    Martin, Nuria
    Cirujano, Francisco G.
    CHEMCATCHEM, 2021, 13 (12) : 2751 - 2765
  • [33] The happiness of the late C-H oxidation
    Harschneck, Tobias
    Kirsch, Stefan F.
    NACHRICHTEN AUS DER CHEMIE, 2010, 58 (01) : 36 - 39
  • [34] Oxidation of unactivated C-H bonds
    Loredo, Leticia
    Perera, Roshan
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2013, 245
  • [35] Progress in Co-Catalyzed C-H Amination
    Sun, Yiming
    Ding, Qifeng
    Yu, Yang
    He, Yide
    Huang, Fei
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2019, 39 (12) : 3363 - 3374
  • [36] Continuous Flow for the Photochemical C-H Amination of Arenes
    Cosgrove, Sebastian C.
    Douglas, Gayle E.
    Raw, Steven A.
    Marsden, Stephen P.
    CHEMPHOTOCHEM, 2018, 2 (10): : 851 - 854
  • [37] Pyridyl Radical Cation for C-H Amination of Arenes
    Rossler, Simon L.
    Jelier, Benson J.
    Tripet, Pascal F.
    Shemet, Andrej
    Jeschke, Gunnar
    Togni, Antonio
    Carreira, Erick M.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (02) : 526 - 531
  • [38] Enantioconvergent Amination of Racemic Tertiary C-H Bonds
    Lang, Kai
    Li, Chaoqun
    Kim, Isaac
    Zhang, X. Peter
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2020, 142 (49) : 20902 - 20911
  • [39] Metal-Free Allylic C-H Amination
    Murakami S.
    Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry, 2023, 81 (03): : 267 - 268
  • [40] Recent advances in electrochemical C-H bond amination
    Liu, Chen
    Liu, Jixuan
    Li, Wenyi
    Lu, Huan
    Zhang, Yunfei
    ORGANIC CHEMISTRY FRONTIERS, 2023, 10 (20) : 5309 - 5330
12345