Synthesis of N-methoxy-1 phosphoryloxy imidates through a copper-catalyzed cross-dehydrogenative coupling of N-methoxylamides with phosphites

被引：6
|
作者：
Deng, Xiangmeng [1 ]
Wang, Ying [1 ]
Liu, Jin-Biao [1 ]
Wan, Changfeng [2 ]
Luo, Nianhua [3 ]
机构：
[1] Jiangxi Univ Sci & Technol, Jiangxi Prov Key Lab Funct Mol Mat Chem, Ganzhou 341000, Peoples R China
[2] Jiangxi Normal Univ, Coll Chem & Chem Engn, Nanchang 330022, Peoples R China
[3] Gannan Med Univ, Sch Pharmaceut Sci, Ganzhou 341000, Peoples R China
来源：
TETRAHEDRON LETTERS | 2022年 / 105卷
基金：
中国国家自然科学基金;
关键词：
Copper catalysis; N-methoxylamide; Phosphite; Cross-dehydrogenative coupling; P-O; H-PHOSPHONATES; GENERAL-METHOD; ALCOHOLS; OXIDES; EFFICIENT; PROTOCOL; AMINES; ESTERS; AMIDES;
D O I：
10.1016/j.tetlet.2022.154049
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Phosphonates are important organic compounds, which are widely used in medicine, materials, agricul-ture and catalysis. In this paper, we report a copper-catalyzed cross-dehydrogenative coupling of N- methoxamides with various phosphites to synthesize a series of N-methoxy-1 phosphoryloxy imidates. O-Functionalization of N-methoxamides has been achieved, and N-functionalization was avoided by employing this methodology. Studies show that the N-methoxy group is essential for the selectivity and activity of the reaction. (c) 2022 Elsevier Ltd. All rights reserved.
引用
收藏
页数：5
相关论文
共 50 条
  • [31] Direct Cross-Dehydrogenative C-N-Coupling of Phenanthridine with 1H-Benzotriazole
    Akulov, A. A.
    Pershin, A. A.
    Kopchuk, D. S.
    Varaksin, M. V.
    Zyryanov, G. V.
    Chupakhin, O. N.
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2023, 59 (07) : 1255 - 1259
  • [32] [(NHC)Yb{N(SiMe3)2}2]-Catalyzed Cross-Dehydrogenative Coupling of Silanes with Amines
    Xie, Weilong
    Hu, Hongfan
    Cui, Chunming
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (44) : 11141 - 11144
  • [33] Zinc(II)-Catalyzed Redox Cross-Dehydrogenative Coupling of Propargylic Amines and Terminal Alkynes for Synthesis of N-Tethered 1,6-Enynes
    Sugiishi, Tsuyuka
    Nakamura, Hiroyuki
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (05) : 2504 - 2507
  • [34] The synthesis of arylcyanamides: a copper-catalyzed consecutive desulfurization and C-N cross-coupling strategy
    Boddapati, S. N. Murthy
    Polam, Naresh
    Mutchu, Baby Ramana
    Bollikolla, Hari Babu
    NEW JOURNAL OF CHEMISTRY, 2018, 42 (02) : 918 - 922
  • [35] Synthesis of Pyrido[1,2-a]benzimidazoles through a Copper-Catalyzed Cascade C-N Coupling Process
    Wu, Zhiqing
    Huang, Qing
    Zhou, Xiangge
    Yu, Lintao
    Li, Zhengkai
    Wu, Di
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2011, 2011 (27) : 5242 - 5245
  • [36] Improved Process for a Copper-Catalyzed C-N Coupling in the Synthesis of Verubecestat
    Phillips, Eric M.
    Reibarkh, Mikhail
    Limanto, John
    Kieu, Minh
    Lekhal, Azzeddine
    Zewge, Daniel
    ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2019, 23 (08) : 1674 - 1678
  • [37] Synthesis of N, N-Dimethyl Benzamide and Benzonitriles through Copper-Catalyzed One-Pot Reaction
    Zhang, Wei
    Hu, Chenxu
    Zhou, Xiangge
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2017, 37 (05) : 1246 - 1251
  • [38] Synthesis of 2-Indolyltetrahydroquinolines by Zinc(II)-Catalyzed Intramolecular Hydroarylation-Redox Cross-Dehydrogenative Coupling of N-Propargylanilines with Indoles
    Li, Guangzhe
    Nakamura, Hiroyuki
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (23) : 6758 - 6761
  • [39] Applications of copper and iron-catalyzed Csp3–Csp3 cross-dehydrogenative coupling in organic synthesis
    Khalifa Z.
    Patel A.B.
    Synthetic Communications, 2023, 53 (20) : 1665 - 1700
  • [40] Copper-Mediated One-Pot Synthesis of Indoles through Sequential Hydroamination and Cross-Dehydrogenative Coupling Reaction
    Sun, Peng
    Yang, Jiaojiao
    Song, Zirui
    Cai, Yichao
    Liu, Yajie
    Chen, Chunxia
    Chen, Xin
    Peng, Jinsong
    SYNTHESIS-STUTTGART, 2020, 52 (01): : 75 - 84
12345