Nickel-catalyzed Amide Transformation via C-N Bond Cleavage

被引:0
|
作者
Nishii, Yuji
机构
关键词
CROSS-COUPLING REACTION; KETONE SYNTHESIS; ORGANOBORON COMPOUNDS; CARBOXYLIC-ACIDS; ESTERS; ANHYDRIDES; ACTIVATION; COMPLEXES;
D O I
10.5059/yukigoseikyokaishi.74.824
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Acyl metal species generated from carboxylic acid derivatives upon treating with low valent transition-metal complexes have been utilized for various catalytic transformations. Recently, it was revealed that a catalyst system of Ni(0)/NHC (N-Heterocyclic Carbene) triggered amide C-N bond cleavage via oxidative addition to afford acyl nickel complexes. The obtained acyl species were further converted into the corresponding esters and ketones in catalytic manner. A proposed reaction mechanism and some synthetic applications are concisely summarized herein.
引用
收藏
页码:824 / 825
页数:2
相关论文
共 50 条
  • [1] Recent advances in nickel-catalyzed amide C-N bond activation
    Dander, Jacob
    Garg, Neil
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2019, 257
  • [2] Cross-Coupling of Amides with Alkylboranes via Nickel-Catalyzed C-N Bond Cleavage
    Liu, Xiangqian
    Hsiao, Chien-Chi
    Guo, Lin
    Rueping, Magnus
    ORGANIC LETTERS, 2018, 20 (10) : 2976 - 2979
  • [3] Nickel-Catalyzed Borylation of Aryl- and Benzyltrimethylammonium Salts via C-N Bond Cleavage
    Hu, Jiefeng
    Sun, Heqing
    Cai, Wangshui
    Pu, Xinghui
    Zhang, Yemin
    Shi, Zhuangzhi
    JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (01): : 14 - 24
  • [4] Nickel-catalyzed activation of Amide C-N bonds
    Baker, Emma
    Garg, Neil
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2016, 252
  • [5] Nickel-catalyzed carboacylation of alkenes via activation of amide C-N bonds
    Walker, James
    Vickerman, Kevin
    Humke, Jenna
    Stanley, Levi
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2017, 253
  • [6] Nickel-catalyzed intermolecular alkene carboacylation via activation of amide C-N bonds
    Kadam, Abhishek
    Metz, Tanner
    Stanley, Levi
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2019, 257
  • [7] Additive-Free Nickel-Catalyzed Debenzylation Reactions via Hydrogenative C-O and C-N Bond Cleavage
    Lange, Saskia
    Formenti, Dario
    Lund, Henrik
    Kreyenschulte, Carsten
    Agostini, Giovanni
    Bartling, Stephan
    Bachmann, Stephan
    Scalone, Michelangelo
    Junge, Kathrin
    Beller, Matthias
    ACS SUSTAINABLE CHEMISTRY & ENGINEERING, 2019, 7 (20) : 17107 - 17113
  • [8] Nickel-Catalyzed Benzylation of Aryl Alkenes with Benzylamines via C-N Bond Activation
    Yu, Hui
    Hu, Bin
    Huang, Hanmin
    JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (22): : 13922 - 13929
  • [9] Nickel-Catalyzed Enantioconvergent Transformation of Anisole Derivatives via Cleavage of C-OMe Bond
    Sun, Tingting
    Zhang, Zishuo
    Su, Yusheng
    Cao, Haiqun
    Zhou, Yu
    Luo, Gen
    Cao, Zhi-Chao
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2023, 145 (29) : 15721 - 15728
  • [10] Nickel-Catalyzed Cross-Coupling of Alkyl Carboxylic Acid Derivatives with Pyridinium Salts via C-N Bond Cleavage
    Pulikottil, Feba Thomas
    Pilli, Ramadevi
    Suku, Rohith Valavil
    Rasappan, Ramesh
    ORGANIC LETTERS, 2020, 22 (08) : 2902 - 2907