Electroreductive Hydroxymethylation of Imines with Ketones To Access fl-Amino Alcohols

被引:10
|
作者
Zeng, Wei-Mei [1 ]
Dong, Wen-Feng [1 ]
He, Yan-Hong [1 ]
Zhao, Ya-Nan [2 ]
Guan, Zhi [1 ]
机构
[1] Southwest Univ, Sch Chem & Chem Engn, Key Lab Appl Chem Chongqing Municipal, Chongqing 400715, Peoples R China
[2] Southwest Univ, Analyt & Testing Ctr, Chongqing 400715, Peoples R China
来源
JOURNAL OF ORGANIC CHEMISTRY | 2023年 / 88卷 / 03期
基金
中国国家自然科学基金;
关键词
%moisture - Alcohol derivatives - Cross-couplings - Direct synthesis - Divided cell - Electrochemical method - Hydroxymethylation - Mechanistic studies - Radical trapping - Synthetic strategies;
D O I
10.1021/acs.joc.2c02674
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
In this article, an electrochemical method for the direct synthesis of fi-amino alcohols from imines and ketones is described. Mechanistic studies, including a radical trapping experiment, electron paramagnetic resonance, cyclic voltammetry, and divided-cell electrolysis experiment, support the radical-involved reductive cross coupling of imines with ketones at the cathode. The use of abundant and easily prepared starting materials, high atom and step-economy, and insensitivity to air and moisture make this synthetic strategy more efficient for the construction of various fi-amino alcohol derivatives.
引用
收藏
页码:1625 / 1634
页数:10
相关论文
共 50 条
  • [41] Synthesis of α-Amino Alcohols via Rh (I)-catalytic Asymmetric Hydrosilylation of Amino Ketones
    Yao, Jin-Shui
    Wu, You-Shi
    Kao Teng Hsueh Hsiao Hua Heush Hsueh Pao/ Chemical Journal of Chinese Universities, 2002, 23 (01):
  • [42] Manganese-Catalyzed Dehydrogenative Cross-Coupling of Secondary Alcohols: Access to Alcohols/Ketones
    Liu Kai
    Xie Jin
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2023, 43 (09) : 3334 - 3336
  • [43] Quinone-catalyzed oxidative deformylation: synthesis of imines from amino alcohols
    Liu, Xinyun
    Phan, Johnny H.
    Haugeberg, Benjamin J.
    Londhe, Shrikant S.
    Clift, Michael D.
    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2017, 13 : 2895 - 2901
  • [44] Amino ketones. I. Synthesis of amino alcohols and 1,3-diamino compounds from beta-amino ketones
    Cromwell, NH
    Wiles, QT
    Schroeder, OC
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1942, 64 : 2432 - 2435
  • [45] Nucleophilic trifluoromethylation of aziridinyl ketones: A convenient access to fluorinated aziridinyl alcohols
    Mloston, Grzegorz
    Obijalska, Emilia
    Ziebacz, Paulina
    Matyszewski, Krzysztof
    Urbaniak, Katarzyna
    Linden, Anthony
    Heimgartner, Heinz
    JOURNAL OF FLUORINE CHEMISTRY, 2013, 156 : 192 - 197
  • [46] Hβ Catalyzed Condensation Reaction Between Aromatic Ketones and Anilines: To Access Ketimines (Imines)
    Amrutham, Vasu
    Mameda, Naresh
    Kodumuri, Srujana
    Chevella, Durgaiah
    Banothu, Rammurthy
    Gajula, Krishna Sai
    Grigor'eva, Nellya Gennadievna
    Nama, Narender
    CATALYSIS LETTERS, 2017, 147 (12) : 2982 - 2986
  • [47] Hβ Catalyzed Condensation Reaction Between Aromatic Ketones and Anilines: To Access Ketimines (Imines)
    Vasu Amrutham
    Naresh Mameda
    Srujana Kodumuri
    Durgaiah Chevella
    Rammurthy Banothu
    Krishna Sai Gajula
    Nellya Gennadievna Grigor’eva
    Narender Nama
    Catalysis Letters, 2017, 147 : 2982 - 2986
  • [48] A New One-Pot, Four-Component Synthesis of 1,2-Amino Alcohols: TiCl3/t-BuOOH-Mediated Radical Hydroxymethylation of Imines
    Clerici, Angelo
    Ghilardi, Alessandra
    Pastori, Nadia
    Punta, Carlo
    Porta, Ornbretta
    ORGANIC LETTERS, 2008, 10 (21) : 5063 - 5066
  • [49] Catalytic enantioselective reduction of prochiral ketones with chiral ferrocenyl amino alcohols
    Chen, WY
    Lu, J
    Shen, ZX
    Zhang, YW
    CHINESE JOURNAL OF CHEMISTRY, 2004, 22 (03) : 306 - 309
  • [50] Chemoenzymatic Synthesis of Enantiopure Amino Alcohols from Simple Methyl Ketones
    Neuburger, Jan Eric
    Gazizova, Alina
    Tiedemann, Sven
    von Langermann, Jan
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2023, 26 (34)