Iron-Catalyzed Selective N-Methylation and N-Formylation of Amines with CO2

被引:59
|
作者
Li, Wen-Duo [1 ,2 ]
Zhu, Dao-Yong [1 ]
Li, Gang [1 ]
Chen, Jie [1 ]
Xia, Ji-Bao [1 ]
机构
[1] Chinese Acad Sci, State Key Lab Oxo Synth & Select Oxidat, Suzhou Res Inst LICP, Lanzhou Inst Chem Phys, Lanzhou 730000, Gansu, Peoples R China
[2] Univ Chinese Acad Sci, Beijing 100049, Peoples R China
关键词
Iron; Mono-phosphine; Carbon dioxide; N-methylation; N-formylation; CARBON-DIOXIDE; HETEROCYCLIC CARBENE; REDUCTIVE FUNCTIONALIZATION; COMPUTATIONAL DESIGN; IONIC LIQUIDS; BASE-METAL; C-O; HYDROGENATION; TRANSFORMATION; HYDROSILANE;
D O I
10.1002/adsc.201900906
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
We herein describe an efficient iron-catalyzed selective N-methylation and N-formylation of amines with CO2 and silane using mono-phosphine as ligand. With commercially available [CpFe(CO)(2)](2) as catalyst, Fe-catalyzed methylation of amines was achieved with triphenylphosphine as a ligand. Using tributylphosphine as a ligand, Fe-catalyzed formylation of amines was realized at a lower temperature. The method was successfully applied in the late-stage methylation and formylation of drug molecules containing amine moiety.
引用
收藏
页码:5098 / 5104
页数:7
相关论文
共 50 条
  • [31] Recyclable polymerized Lewis acid poly-BPh(C6F5)2 catalyzed selective N-formylation and N-methylation of amines with carbon dioxide and phenylsilanes
    Zhai, Gaowen
    Liu, Qiang
    Ji, Jialan
    Wu, Youting
    Geng, Jiao
    Hu, Xingbang
    JOURNAL OF CO2 UTILIZATION, 2022, 61
  • [32] Mechanism of iron complexes catalyzed in the N-formylation of amines with CO2 and H2: the superior performance of N-H ligand methylated complexes
    Shen, Xinyu
    Wang, Wenjuan
    Wang, Qiong
    Liu, Jianbiao
    Huang, Fang
    Sun, Chuanzhi
    Yang, Chong
    Chen, Dezhan
    PHYSICAL CHEMISTRY CHEMICAL PHYSICS, 2021, 23 (31) : 16675 - 16689
  • [33] A supported pyridylimine-cobalt catalyst for N-formylation of amines using CO2
    Akhtar, Naved
    Chauhan, Manav
    Gupta, Poorvi
    Antil, Neha
    Manna, Kuntal
    DALTON TRANSACTIONS, 2023, 52 (42) : 15384 - 15393
  • [34] Catalyst-free N-methylation of amines using CO2
    Niu, Huiying
    Lu, Lijun
    Shi, Renyi
    Chiang, Chien-Wei
    Lei, Aiwen
    CHEMICAL COMMUNICATIONS, 2017, 53 (06) : 1148 - 1151
  • [35] Nickel-(II)-Catalyzed N-Formylation and N-Acylation of Amines
    Sonawane, Rahul B.
    Rasal, Nishant K.
    Jagtap, Sangeeta V.
    ORGANIC LETTERS, 2017, 19 (08) : 2078 - 2081
  • [36] N-formylation of amines with CO2 by using Zr-based metal-organic frameworks: Contribution of defect sites of MOFs to N-formylation
    Yoo, Dong Kyu
    Jhung, Sung Hwa
    APPLIED CATALYSIS A-GENERAL, 2023, 659
  • [37] Well-Defined Phosphine-Free Iron-Catalyzed N-Ethylation and N-Methylation of Amines with Ethanol and Methanol
    Lator, Alexis
    Gaillard, Sylvain
    Poater, Albert
    Renaud, Jean-Luc
    ORGANIC LETTERS, 2018, 20 (19) : 5985 - 5990
  • [38] Phosphite-imidazole catalyzed N-formylation and N-acylation of amines
    Kaboudin, Babak
    Esfandiari, Hesam
    Kakavand, Meysam
    Sohrabi, Masoumeh
    Amirkhiz, Elahe Yousefian
    Neshat, Abdollah
    Kawazoe, Teru
    Fukaya, Haruhiko
    Yanai, Hikaru
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2023, 21 (40) : 8182 - 8189
  • [39] Iron-Rich Natural Mineral Gibeon Meteorite Catalyzed N-formylation of Amines using CO2 as the C1 Source
    Gopakumar, Aswin
    Akcok, Ismail
    Lombardo, Loris
    Le Formal, Florian
    Magrez, Arnaud
    Sivula, Kevin
    Dyson, Paul J.
    CHEMISTRYSELECT, 2018, 3 (37): : 10271 - 10276
  • [40] Bis(N-Heterocyclic Carbene) Manganese(I) Complexes in Catalytic N-Formylation/N-Methylation of Amines Using Carbon Dioxide and Phenylsilane
    Masaro, Chiara
    Meloni, Giammarco
    Baron, Marco
    Graiff, Claudia
    Tubaro, Cristina
    Royo, Beatriz
    CHEMISTRY-A EUROPEAN JOURNAL, 2023, 29 (67)