Dual Intermolecular Allylic C-H Functionalization of the Tetrasubstituted Alkene Scaffold

被引：3
|
作者：
Martinez, Claudio [1 ]
Muniz, Kilian [1 ,2 ]
机构：
[1] Inst Chem Res Catalonia ICIQ, Ave Paisos Catalans 16, Wuhan 430070, Peoples R China
[2] ICREA, Pg Lluis Companys 23, Barcelona 08010, Spain
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2018年 / 2018卷 / 10期
关键词：
Alkenes; Allylic compounds; Oxidation; Amination; Chlorine; Dienes; BROMINE-CATALYZED AZIRIDINATION; METAL-FREE AZIRIDINATION; ENOL ETHER CHEMISTRY; CHLORAMINE-T; BOND FUNCTIONALIZATION; N-BROMOSUCCINIMIDE; AMINATION; OLEFINS; IODINE; OXIDATION;
D O I：
10.1002/ejoc.201701624
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Activation of chloramine-T (TsNNaCl) with a BrOnsted acid generates an active reagent for the double allylic C-H functionalization of tetrasubstituted alkenes in an intermolecular manner. The reaction generates a carbon-nitrogen and a carbon-chlorine bond, and proceeds with complete regio- and chemoselectivity. A total of 14 examples demonstrate the applicability of the dual C-H functionalization process. The mechanism involves the intermediacy of a 1,3-butadiene derivative; 1,3-butadienes can also be used directly as substrates.
引用
收藏
页码：1248 / 1254
页数：7
相关论文
共 50 条
  • [21] Asymmetric intermolecular allylic C-H amination of alkenes with aliphatic amines
    Cheung, Kelvin Pak Shing
    Fang, Jian
    Mukherjee, Kallol
    Mihranyan, Andranik
    Gevorgyan, Vladimir
    SCIENCE, 2022, 378 (6625) : 1207 - 1213
  • [22] A Catalytic, Bronsted Base Strategy for Intermolecular Allylic C-H Amination
    Reed, Sean A.
    Mazzotti, Anthony R.
    White, M. Christina
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (33) : 11701 - 11706
  • [23] Reversible alkene binding and allylic C-H activation with an aluminium(i) complex
    Bakewell, Clare
    White, Andrew J. P.
    Crimmin, Mark R.
    CHEMICAL SCIENCE, 2019, 10 (08) : 2452 - 2458
  • [24] Allylic C-H functionalization via group 9 π-allyl intermediates
    Nelson, Taylor A. F.
    Hollerbach, Michael R.
    Blakey, Simon B.
    DALTON TRANSACTIONS, 2020, 49 (40) : 13928 - 13935
  • [25] Palladium-Catalyzed Allylic C-H Bond Functionalization of Olefins
    Liu, Guosheng
    Wu, Yichen
    C-H ACTIVATION, 2010, 292 : 195 - 209
  • [26] Enantioselective Intermolecular C-H Functionalization of Allylic and Benzylic sp3 C-H Bonds Using N-Sulfonyl-1,2,3-triazoles
    Kubiak, Robert W., II
    Mighion, Jeffrey D.
    Wilkerson-Hill, Sidney M.
    Alford, Joshua S.
    Yoshidomi, Tetsushi
    Davies, Huw M. L.
    ORGANIC LETTERS, 2016, 18 (13) : 3118 - 3121
  • [27] Dual C-F/C-H functionalization unveiled
    Ritter, Steve
    CHEMICAL & ENGINEERING NEWS, 2016, 94 (10) : 12 - 12
  • [28] Biocatalytic, Intermolecular C-H Bond Functionalization for the Synthesis of Enantioenriched Amides
    Athavale, Soumitra V.
    Gao, Shilong
    Liu, Zhen
    Mallojjala, Sharath Chandra
    Hirschi, Jennifer S.
    Arnold, Frances H.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2021, 60 (47) : 24864 - 24869
  • [29] Cobalt(III)-Catalyzed Enantioselective Intermolecular Carboamination by C-H Functionalization
    Ozols, Kristers
    Onodera, Shunsuke
    Wozniak, Lukasz
    Cramer, Nicolai
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2021, 60 (02) : 655 - 659
  • [30] Enantioselective C-H Bond Functionalization Triggered by Radical Trifluoromethylation of Unactivated Alkene
    Yu, Peng
    Lin, Jin-Shun
    Li, Lei
    Zheng, Sheng-Cai
    Xiong, Ya-Ping
    Zhao, Li-Jiao
    Tan, Bin
    Liu, Xin-Yuan
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (44) : 11890 - 11894
12345