Copper-Catalyzed Borrowing Hydrogen Reaction for α-Alkylation of Amides with Alcohols

被引：2
|
作者：
Xia, Qiuling [1 ,2 ]
Miao, Yulong [2 ]
Hu, Yue [2 ]
Xie, Yinjun [2 ]
Luo, Junfei [1 ]
机构：
[1] Ningbo Univ, Inst Mass Spectrometry, Zhejiang Engn Res Ctr Adv Mass Spectrometry & Clin, Sch Mat Sci & Chem Engn, Ningbo 315211, Peoples R China
[2] Chinese Acad Sci, Ningbo Inst Mat Technol & Engn, Key Lab Adv Fuel Cells & Electrolyzers & Technol Z, Ningbo 315201, Peoples R China
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2024年 / 89卷 / 13期
基金：
中国国家自然科学基金;
关键词：
UNACTIVATED AMIDES; C-ALKYLATION; KETONES; ESTERS; PHARMACOKINETICS; PAZINACLONE; ACETAMIDES; LIGAND;
D O I：
10.1021/acs.joc.4c00404
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
We report the first example of copper-catalyzed alpha-alkylation of acetamides with alcohols via a borrowing hydrogen strategy. Catalyzed by the in situ-generated copper particles, acetamides and various substituted benzyl or alkyl alcohols were transformed into functionalized amides in good yields with excellent selectivity. Compared with previous work, this process is simple using commercially available Cu(OAc)(2) as a precatalyst, without an additional ligand or a metal complex, and easier. Mechanistic studies revealed that aldehyde and alpha,beta-unsaturated amides were the intermediates of this reaction and also disclosed the role of copper in alcohol dehydrogenation and C=C bond hydrogenation.
引用
收藏
页码：9654 / 9660
页数：7
相关论文
共 50 条
  • [21] Ruthenium- and Copper-Catalyzed Enantioselective Propargylic Alkylation of Propargylic Alcohols with β-Keto Phosphonates
    Motoyama, Kazuki
    Ikeda, Masahiro
    Miyake, Yoshihiro
    Nishibayashi, Yoshiaki
    ORGANOMETALLICS, 2012, 31 (08) : 3426 - 3430
  • [22] Copper-Catalyzed N-Alkylation of Sulfonamides with Benzylic Alcohols: Catalysis and Mechanistic Studies
    Cui, Xinjiang
    Shi, Feng
    Tse, Man Kin
    Goerdes, Dirk
    Thurow, Kerstin
    Beller, Matthias
    Deng, Youquan
    ADVANCED SYNTHESIS & CATALYSIS, 2009, 351 (17) : 2949 - 2958
  • [23] Copper-Catalyzed Alkoxycarbonylation of Alkanes with Alcohols
    Li, Yahui
    Wang, Changsheng
    Zhu, Fengxiang
    Wang, Zechao
    Dixneuf, Pierre H.
    Wu, Xiao-Feng
    CHEMSUSCHEM, 2017, 10 (07) : 1341 - 1345
  • [24] Copper-catalyzed tandem reaction between imines and alcohols leading to indoles
    Kamijo, S
    Sasaki, Y
    Yamamoto, Y
    TETRAHEDRON LETTERS, 2004, 45 (01) : 35 - 38
  • [25] Copper-catalyzed arylation of β-amino alcohols
    Job, GE
    Buchwald, L
    ORGANIC LETTERS, 2002, 4 (21) : 3703 - 3706
  • [26] Copper-Catalyzed Dehydration of Primary Amides to Nitriles
    Enthaler, Stephan
    Weidauer, Maik
    CATALYSIS LETTERS, 2011, 141 (08) : 1079 - 1085
  • [27] COPPER-CATALYZED HYDROLYSIS OF SOME ESTERS AND AMIDES
    AGREN, A
    EKENVED, G
    NILSSON, SO
    SVENSJO, E
    ACTA PHARMACEUTICA SUECICA, 1965, 2 (06): : 421 - &
  • [28] Copper-Catalyzed Silylperoxidation Reaction of α,β-Unsaturated Ketones, Esters, Amides, and Conjugated Enynes
    Lan, Yun
    Chang, Xi-Hao
    Fan, Pei
    Shan, Cui-Cui
    Liu, Zi-Bai
    Loh, Teck-Peng
    Xu, Yun-He
    ACS CATALYSIS, 2017, 7 (10): : 7120 - 7125
  • [29] Copper-Catalyzed Carbonylative Coupling of Cycloalkanes and Amides
    Li, Yahui
    Dong, Kaiwu
    Zhu, Fengxiang
    Wang, Zechao
    Wu, Xiao-Feng
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (25) : 7227 - 7230
  • [30] Borrowing hydrogen alkylation of indenes with alcohols by manganese pincer complex
    Geng, Shuaihu
    Yang, Jue
    Lugovski, Aleksander A.
    Liu, Weiping
    JOURNAL OF CATALYSIS, 2025, 445
12345