Nickel-catalyzed Amide Transformation via C-N Bond Cleavage

被引：0
|
作者：
Nishii, Yuji
机构：
来源：
JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN | 2016年 / 74卷 / 08期
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
  • [41] Nickel-Catalyzed Synthesis of Primary Aryl and Heteroaryl Amines via C-O Bond Cleavage
    Yue, Huifeng
    Guo, Lin
    Liu, Xiangqian
    Rueping, Magnus
    ORGANIC LETTERS, 2017, 19 (07) : 1788 - 1791
  • [42] Nickel-Catalyzed, Stereospecific C-C and C-B Cross-Couplings via C-N and C-O Bond Activation
    Xu, Jianyu
    Bercher, Olivia P.
    Talley, Michael R.
    Watson, Mary P.
    ACS CATALYSIS, 2021, 11 (03) : 1604 - 1612
  • [43] Palladium-Catalyzed Hydroaminocarbonylation of Alkynes with Tertiary Amines via C-N Bond Cleavage
    Gao, Bao
    Huang, Hanmin
    ORGANIC LETTERS, 2017, 19 (22) : 6260 - 6263
  • [44] I 2 -Catalyzed Oxidative Acylation of Tertiary Amines via C-N Bond Cleavage
    Ge, Xin
    Lei, Ping
    Su, Qin
    Pan, Ying-Ming
    Ablajan, Keyume
    SYNTHESIS-STUTTGART, 2024, 56 (10): : 1648 - 1656
  • [45] Nickel-Catalyzed Cross Couplings of Benzylic Ammonium Salts and Boronic Acids: Stereospecific Formation of Diarylethanes via C-N Bond Activation
    Maity, Prantik
    Shacklady-McAtee, Danielle M.
    Yap, Glenn P. A.
    Sirianni, Eric R.
    Watson, Mary P.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (01) : 280 - 285
  • [46] Nickel-Catalyzed Amide Bond Formation from Methyl Esters
    Ben Halima, Taoufik
    Masson-Makdissi, Jeanne
    Newman, Stephen G.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (39) : 12925 - 12929
  • [47] Amide/Ester Cross-Coupling via C-N/C-H Bond Cleavage: Synthesis of β-Ketoesters
    Chen, Jiajia
    Joseph, Devaneyan
    Xia, Yuanzhi
    Lee, Sunwoo
    JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (08): : 5943 - 5953
  • [48] Nitrogenation of Amides via C-C and C-N Bond Cleavage
    Zhu, Ming -Hui
    Cheng, Zengrui
    Wei, Jialiang
    Tan, Hui
    Jiao, Ning
    CCS CHEMISTRY, 2023, 5 (05): : 1061 - 1068
  • [49] Ni-Catalyzed Intermolecular Carboacylation of Internal Alkynes via Amide C-N Bond Activation
    Koeritz, Mason T.
    Burgett, Russell W.
    Kadam, Abhishek A.
    Stanley, Levi M.
    ORGANIC LETTERS, 2020, 22 (15) : 5731 - 5736
  • [50] Zinc-catalyzed transamidation and esterification of N-benzoyl cytosine via C-N bond cleavage
    Gaware, Sujeet
    Chatterjee, Rana
    Kapdi, Anant R. R.
    Dandela, Rambabu
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2023, 21 (25) : 5176 - 5180
12345