Iron-Catalyzed Borrowing Hydrogen C-Alkylation of Oxindoles with Alcohols

被引:61
|
作者
Dambatta, Mubarak B. [1 ]
Polidano, Kurt [1 ]
Northey, Alexander D. [1 ]
Williams, Jonathan M. J. [2 ]
Morrill, Louis C. [1 ]
机构
[1] Cardiff Univ, Sch Chem, Cardiff Catalysis Inst, Main Bldg,Pk Pl, Cardiff CF10 3AT, S Glam, Wales
[2] Univ Bath, Dept Chem, Bath BA2 7AY, Avon, England
基金
英国工程与自然科学研究理事会;
关键词
alcohols; alkylation; borrowing hydrogen; iron catalysis; oxindoles; ONE-POT SYNTHESIS; N BOND FORMATION; ALPHA-ALKYLATION; ENANTIOSELECTIVE FUNCTIONALIZATION; TRICARBONYL COMPLEXES; ORGANIC-SYNTHESIS; NATURAL-PRODUCTS; RUTHENIUM; AMINES; KETONES;
D O I
10.1002/cssc.201900799
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A general and efficient iron-catalyzed C-alkylation of oxindoles has been developed. This borrowing hydrogen approach employing a (cyclopentadienone)iron carbonyl complex (2 mol %) exhibited a broad reaction scope, allowing benzylic and simple primary and secondary aliphatic alcohols to be employed as alkylating agents. A variety of oxindoles underwent selective mono-C3-alkylation in good-to-excellent isolated yields (28 examples, 50-92 % yield, 79 % average yield).
引用
收藏
页码:2345 / 2349
页数:5
相关论文
共 50 条
  • [41] Photoinduced iron-catalyzed C-H alkylation of polyolefins
    Zhang, Zongnan
    Zhang, Yanfeng
    Zeng, Rong
    CHEMICAL SCIENCE, 2023, 14 (35) : 9374 - 9379
  • [42] Borrowing Hydrogen in Water and Ionic Liquids: Iridium-Catalyzed Alkylation of Amines with Alcohols
    Saidi, Ourida
    Blacker, A. John
    Lamb, Gareth W.
    Marsden, Stephen P.
    Taylor, James E.
    Williams, Jonathan M. J.
    ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2010, 14 (04) : 1046 - 1049
  • [43] Enantioselective Iron-Catalyzed Azidation of β-Keto Esters and Oxindoles
    Deng, Qing-Hai
    Bleith, Tim
    Wadepohl, Hubert
    Gade, Lutz H.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (14) : 5356 - 5359
  • [44] C-Alkylation by Hydrogen Autotransfer Reactions
    Obora, Yasushi
    TOPICS IN CURRENT CHEMISTRY, 2016, 374 (02)
  • [45] Iron-Catalyzed Synthesis of Oxindoles: Application to the Preparation of Pyrroloindolines
    Correia, Valquirio G.
    Abreu, Juliana C.
    Barata, Caio A. E.
    Andrade, Leandro H.
    ORGANIC LETTERS, 2017, 19 (05) : 1060 - 1063
  • [46] C-Alkylation of Ketones and Related Compounds by Alcohols: Transition-Metal-Catalyzed Dehydrogenation
    Huang, Fei
    Liu, Zhuqing
    Yu, Zhengkun
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (03) : 862 - 875
  • [47] General and Mild Cobalt-Catalyzed C-Alkylation of Unactivated Amides and Esters with Alcohols
    Deibl, Nicklas
    Kempe, Rhett
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (34) : 10786 - 10789
  • [48] C-Alkylation by Hydrogen Autotransfer Reactions
    Yasushi Obora
    Topics in Current Chemistry, 2016, 374
  • [49] A novel acid-catalyzed C5-alkylation of oxindoles using alcohols
    Reddy, Chada Raji
    Jithender, Enukonda
    Krishna, Gaddam
    Reddy, Gunreddy Venkat
    Jagadeesh, Bharatam
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2011, 9 (10) : 3940 - 3947
  • [50] Blue-light induced iron-catalyzed chemoselective α-alkylation and α-olefination of arylacetonitriles with alcohols
    Song, Dingguo
    Wang, Shiliang
    Huang, Weiwei
    Chen, Rong
    Hu, Fangyuan
    Cheng, Lingxin
    Zhao, Xianghua
    Ling, Fei
    Zhong, Weihui
    ORGANIC CHEMISTRY FRONTIERS, 2023, 10 (23) : 5908 - 5915