Efficient N-methylation of primary amides using methanol under Mn (I)-catalysis

被引:0
|
作者
Babu, Reshma [1 ]
Padhy, Smruti Rekha [2 ]
Balaraman, Ekambaram [1 ,2 ]
机构
[1] Indian Inst Sci Educ & Res IISER Tirupati, Dept Chem, Tirupati 517507, India
[2] IISER Tirupati, DST Nodal Ctr APIs & KSM Prod, Therapeut Chem Program, Tirupati 517619, India
关键词
Alcohol; Amides; Acceptorless dehydrogenation; Homogeneous catalysis; Manganese; SUSTAINABLE SYNTHESIS; BORROWING HYDROGEN; SECONDARY ALCOHOLS; AMINES; ALKYLATION; DEHYDROGENATION; H-2; FORMYLATION; KETONES; ESTERS;
D O I
10.1016/j.tet.2025.134535
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Herein, we report the use of methanol, a renewable, cost-effective, and easily handled reagent, for the highly selective N-methylation of amides under mild conditions. The reaction is catalyzed by a well-defined Mn-PNP pincer complex and proceeds via the borrowing hydrogen strategy (BHS). This method exhibits broad functional group tolerance and utilizes methanol as a methylating agent, demonstrating exceptional monoselectivity for amides, which enhances its practical appeal. Additionally, a series of control experiments were conducted to provide deeper mechanistic insights into the transformation.
引用
收藏
页数:10
相关论文
共 50 条
  • [41] A practical method for N-methylation of indoles using dimethyl carbonate
    Jiang, XL
    Tiwari, A
    Thompson, M
    Chen, ZH
    Cleary, TP
    Lee, TBK
    ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2001, 5 (06) : 604 - 608
  • [42] N-METHYLATION - POTENTIAL MECHANISM FOR METABOLIC-ACTIVATION OF CARCINOGENIC PRIMARY ARYLAMINES
    ZIEGLER, DM
    ANSHER, SS
    NAGATA, T
    KADLUBAR, FF
    JAKOBY, WB
    PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1988, 85 (08) : 2514 - 2517
  • [43] Selective mono N-methylation of anilines with methanol catalyzed by rhenium complexes: An experimental and theoretical study
    Wei, Duo
    Sadek, Omar
    Dorcet, Vincent
    Roisnel, Thierry
    Darcel, Christophe
    Gras, Emmanuel
    Clot, Eric
    Sortais, Jean-Baptiste
    JOURNAL OF CATALYSIS, 2018, 366 : 300 - 309
  • [44] Homogeneous Catalysis in N-Formylation/N-Methylation Utilizing Carbon Dioxide as the C1 Source
    Dutta, Indranil
    Gholap, Sandeep Suryabhan
    Rahman, Mohammad Misbahur
    Tan, Davin
    Zhang, Lili
    Dighe, Shashikant U.
    Huang, Kuo-Wei
    CHEMISTRY-AN ASIAN JOURNAL, 2024, 19 (22)
  • [45] Selective N-methylation of pyrazolone with methanol by use of ZrO2 catalyst in the liquid phase
    Shinoda, S
    Shima, S
    Yamakawa, T
    SYNLETT, 2000, (06) : 809 - 810
  • [46] A review on recent developments in N-methylation using CO2
    Lin, Shanshan
    Liu, Jianguo
    Ma, Longlong
    JOURNAL OF CO2 UTILIZATION, 2021, 54
  • [47] Air-tolerant direct reductive N-methylation of amines using formic acid via simple inorganic base catalysis
    Huang, Yan
    Deng, Wei
    Lin, Bo-Lin
    CHINESE CHEMICAL LETTERS, 2020, 31 (01) : 111 - 114
  • [48] Air-tolerant direct reductive N-methylation of amines using formic acid via simple inorganic base catalysis
    Yan Huang
    Wei Deng
    Bo-Lin Lin
    ChineseChemicalLetters, 2020, 31 (01) : 111 - 114
  • [49] Photoinduced N-Methylation and N-Sulfonylation of Azobenzenes with DMSO Under Mild Reaction Conditions
    Xu, Ning
    Zhang, Yan
    Chen, Wei
    Li, Pinhua
    Wang, Lei
    ADVANCED SYNTHESIS & CATALYSIS, 2018, 360 (06) : 1199 - 1208
  • [50] USE OF ZINC BOROHYDRIDE IN REDUCTIVE AMINATION - AN EFFICIENT AND MILD METHOD FOR N-METHYLATION OF AMINES
    BHATTACHARYYA, S
    CHATTERJEE, A
    DUTTACHOWDHURY, SK
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1994, (01): : 1 - 2