Copper-catalyzed C-P cross-coupling of arylmethyl quaternary ammonium salts via C-N bond cleavage

被引:9
|
作者
Li, Nutao [1 ]
Chen, Feng [1 ]
Wang, Guanghui [1 ]
Zeng, Qingle [1 ]
机构
[1] Chengdu Univ Technol, Coll Mat Chem & Chem Engn, State Key Lab Geohazard Prevent & Geoenvironm Pro, Chengdu 610059, Sichuan, Peoples R China
来源
MONATSHEFTE FUR CHEMIE | 2020年 / 151卷 / 01期
关键词
Copper; Cross-coupling; C-N cleavage; Arylmethyl quaternary ammonium salts; Dialkylphosphine oxides; ARYLBORONIC ACIDS; ANTAGONIST; FOSTEDIL; OXIDES;
D O I
10.1007/s00706-019-02535-y
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A ligand-free copper-catalyzed C-P cross-coupling reaction of arylmethyl quaternary ammonium salts and diarylphosphine oxides in air is developed. Arylmethyl quaternary ammonium salts with various functional groups and a variety of dialkyl- and diarylphosphine oxides afford C-P cross-coupling products with good yields. This protocol requires no inert atmosphere, no ligand, and simple operation steps.
引用
收藏
页码:99 / 106
页数:8
相关论文
共 50 条
  • [31] Copper-Catalyzed C-S Coupling of Quaternary Ammonium Salts and Dialkylcarbamodithioic Acid Salts
    Chen, Hongyi
    Zhang, Qiaoling
    Zheng, Wenting
    Yang, Hongqin
    Zeng, Qingle
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 9 (05) : 773 - 777
  • [32] Copper-catalyzed C-N cross-coupling for construction of alkylated N-cyanamide derivatives via nitrogen umpolung
    Wan, Yanjun
    Zhang, Harriet K.
    Qian, Jin
    Aliyu, Muinat A.
    Norton, Jack R.
    CHEM, 2024, 10 (08):
  • [33] Copper-Catalyzed C-P Coupling through Decarboxylation
    Hu, Jie
    Zhao, Ning
    Yang, Bin
    Wang, Ge
    Guo, Li-Na
    Liang, Yong-Min
    Yang, Shang-Dong
    CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (20) : 5516 - 5521
  • [34] Oxalamide/Amide Ligands: Enhanced and Copper-Catalyzed C-N Cross-Coupling for Triarylamine Synthesis
    Li, Sasa
    Huang, Xia
    Gao, Yunlong
    Jin, Jian
    ORGANIC LETTERS, 2022, 24 (31) : 5817 - 5824
  • [35] Mechanistic Study of Copper-Catalyzed Decarboxylative C-N Cross-Coupling with Hypervalent Iodine Oxidant
    Yang, Yi-Nuo
    Jiang, Ju-Long
    Shi, Jing
    ORGANOMETALLICS, 2017, 36 (11) : 2081 - 2087
  • [36] A domino copper-catalyzed C-N and C-O cross-coupling for the conversion of primary amides into benzoxazoles
    Altenhoff, G
    Glorius, F
    ADVANCED SYNTHESIS & CATALYSIS, 2004, 346 (13-15) : 1661 - 1664
  • [37] A domino copper-catalyzed C-N and C-O cross-coupling for the conversion of primary Amides into oxazoles
    Schuh, Kerstin
    Glorius, Frank
    SYNTHESIS-STUTTGART, 2007, (15): : 2297 - 2306
  • [38] Cross-coupling polycondensation via C–O or C–N bond cleavage
    Ze-Kun Yang
    Ning-Xin Xu
    Ryo Takita
    Atsuya Muranaka
    Chao Wang
    Masanobu Uchiyama
    Nature Communications, 9
  • [39] 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
  • [40] Copper-promoted C-N bond cross-coupling with phenylstannane
    Lam, PYS
    Vincent, G
    Bonne, D
    Clark, CG
    TETRAHEDRON LETTERS, 2002, 43 (16) : 3091 - 3094