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
来源：
ADVANCED SYNTHESIS & CATALYSIS | 2019年 / 361卷 / 22期
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
  • [1] DBU-Catalyzed Selective N-Methylation and N-Formylation of Amines with CO2 and Polymethylhydrosiloxane
    Li, Gang
    Chen, Jie
    Zhu, Dao-Yong
    Chen, Ye
    Xia, Ji-Bao
    ADVANCED SYNTHESIS & CATALYSIS, 2018, 360 (12) : 2364 - 2369
  • [2] Phosphonium-Salt-Catalyzed N-Methylation and N-Formylation of Amines with CO2
    Ren, Changyue
    Spannenberg, Anke
    Werner, Thomas
    ACS SUSTAINABLE CHEMISTRY & ENGINEERING, 2024, 12 (29): : 10969 - 10977
  • [3] Copper catalysis: ligand-controlled selective N-methylation or N-formylation of amines with CO2 and phenylsilane
    Li, Xue-Dong
    Xia, Shu-Mei
    Chen, Kai-Hong
    Liu, Xiao-Fang
    Li, Hong-Ru
    He, Liang-Nian
    GREEN CHEMISTRY, 2018, 20 (21) : 4853 - 4858
  • [4] Dehydrogenative N-formylation and N-methylation of amines catalyzed by ruthenium pincer complex
    Choi, Geunho
    Kim, Seung Hyo
    Hong, Soon Hyeok
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2017, 253
  • [5] Selective Iron-Catalyzed N-Formylation of Amines using Dihydrogen and Carbon Dioxide
    Jayarathne, Upul
    Hazari, Nilay
    Bernskoetter, Wesley H.
    ACS CATALYSIS, 2018, 8 (02): : 1338 - 1345
  • [6] Mn-Catalyzed Selective Double and Mono-N-Formylation and N-Methylation of Amines by using CO2
    Huang, Zijun
    Jiang, Xiaolin
    Zhou, Shaofang
    Yang, Peiju
    Du, Chen-Xia
    Li, Yuehui
    CHEMSUSCHEM, 2019, 12 (13) : 3054 - 3059
  • [7] Catalyst-free selective N-formylation and N-methylation of amines using CO2 as a sustainable C1 source
    Zou, Qizhuang
    Long, Guangcai
    Zhao, Tianxiang
    Hu, Xingbang
    GREEN CHEMISTRY, 2020, 22 (04) : 1134 - 1138
  • [8] A polymeric ionic liquid catalyst for the N-formylation and N-methylation of amines using CO2/PhSiH3
    Gopakumar, Aswin
    Lombardo, Loris
    Fei, Zhaofu
    Shyshkanov, Serhii
    Vasilyev, Dmitry
    Chidambaram, Arunraj
    Stylianou, Kyriakos
    Zuttel, Andreas
    Dyson, Paul J.
    JOURNAL OF CO2 UTILIZATION, 2020, 41
  • [9] Selective N-Formylation and N-Methylation of Amines Using Methanol as a Sustainable C1 Source
    Choi, Geunho
    Hong, Soon Hyeok
    ACS SUSTAINABLE CHEMISTRY & ENGINEERING, 2019, 7 (01) : 716 - 723
  • [10] Ag-Nanocatalysts Based on Porous Organic Polymers in Chemical Fixation of CO2 for the N-Methylation and N-Formylation of Amines
    Chakrabortty, Pekham
    Kumar, Susmitha
    Chowdhury, Avik
    Khan, Aslam
    Bhaumik, Asim
    Islam, Sk Manirul
    CHEMCATCHEM, 2024, 16 (05)
12345