Cobalt-Catalyzed Esterification of Amides

被引:91
|
作者
Bourne-Branchu, Yann [1 ]
Gosmini, Corinne [1 ]
Danoun, Gregory [1 ]
机构
[1] Univ Paris Saclay, CNRS, Ecole Polytech, LCM, F-91128 Palaiseau, France
关键词
amides; cobalt; cross-coupling; esterification; homogeneous catalysis; N-C CLEAVAGE; CHEMOSELECTIVE KETONE SYNTHESIS; CROSS-COUPLING REACTIONS; CARBON-CARBON BONDS; TWISTED AMIDES; TERTIARY AMIDE; GENERAL-METHOD; ACTIVATION; FUNCTIONALIZATION; TRANSAMIDATION;
D O I
10.1002/chem.201702608
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The first cobalt-catalyzed amide activation of N-Boc-amides, and their conversion into esters, is reported here. This new methodology presents a very practical process that does not require an inert atmosphere, uses an inexpensive cobalt catalyst, and proceeds under mild reaction conditions. This catalytic system has a broad substrate scope and has been shown to be highly efficient, with catalyst loadings as low as 1 mol%.
引用
收藏
页码:10043 / 10047
页数:5
相关论文
共 50 条
  • [1] Homogeneous cobalt-catalyzed deoxygenative hydrogenation of amides to amines
    Papa, Veronica
    Cabrero-Antonino, Jose R.
    Spannenberg, Anke
    Junge, Kathrin
    Beller, Matthias
    CATALYSIS SCIENCE & TECHNOLOGY, 2020, 10 (18) : 6125 - 6137
  • [2] Cobalt-Catalyzed Aminocarbonylation of Alkyl Tosylates: Stereospecific Synthesis of Amides
    Sargent, Brendon T.
    Alexanian, Erik J.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (28) : 9533 - 9536
  • [3] Cobalt-catalyzed esterification-peroxidation of α-diazoesters: access to α-acyloxy esters
    Chen, Rongxiang
    Ma, Guoyang
    Zhang, Jinju
    Wang, Zhan-Yong
    Xu, Shaohong
    Wang, Kai-Kai
    NEW JOURNAL OF CHEMISTRY, 2023, 47 (04) : 2086 - 2089
  • [4] Cobalt-Catalyzed Cross-Coupling of α-Bromo Amides with Grignard Reagents
    Barde, E.
    Guerinot, A.
    Cossy, J.
    ORGANIC LETTERS, 2017, 19 (22) : 6068 - 6071
  • [5] Cobalt-Catalyzed Perfluoroalkylation of Quinoline Amides at the C5 Position
    Suo, Jian-Feng
    Zhao, Xue-Mei
    Zhang, Kai-Xin
    Zhou, Sheng-Li
    Niu, Jun-Long
    Song, Mao-Ping
    SYNTHESIS-STUTTGART, 2017, 49 (17): : 3916 - 3924
  • [6] Cobalt-catalyzed synthesis of amides from alkenes and amines promoted by light
    Faculak, Mason S.
    Veatch, Alexander M.
    Alexanian, Erik J.
    SCIENCE, 2024, 383 (6678) : 77 - 81
  • [7] Cobalt-Catalyzed Cyclization of Aliphatic Amides and Terminal Alkynes with Silver-Cocatalyst
    Zhang, Jitan
    Chen, Hui
    Lin, Cong
    Liu, Zhanxiang
    Wang, Chen
    Zhang, Yuhong
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (40) : 12990 - 12996
  • [8] Diastereoselective intermolecular cobalt-catalyzed reductive aldol reactions of α,β-unsaturated Amides with ketones
    Lumby, Ralph J. R.
    Joensuu, Pekka M.
    Lam, Hon Wai
    ORGANIC LETTERS, 2007, 9 (21) : 4367 - 4370
  • [9] Cobalt-catalyzed direct α-hydroxymethylation of amides with methanol as a C1 source
    Ma, Ben
    Sun, Rongxia
    Yang, Jingya
    CHEMICAL COMMUNICATIONS, 2022, 58 (09) : 1382 - 1385
  • [10] Cobalt-Catalyzed Allylation of Amides with Styrenes Using DMSO as Both the Solvent and the α-Methylene Source
    Zhang, Xu
    Zhou, Zhi
    Xu, Huiying
    Xu, Xuefeng
    Yu, Xiyong
    Yi, Wei
    ORGANIC LETTERS, 2019, 21 (18) : 7248 - 7253