Ruthenium-Catalyzed Transfer Hydrogenation of Amino- and Amido-Substituted Acetophenones

被引:16
作者
Watson, Andrew J. A. [1 ]
Fairbanks, Antony J. [1 ]
机构
[1] Univ Canterbury, Dept Chem, Christchurch 8041, New Zealand
关键词
Ruthenium; Homogeneous catalysis; Hydrogen transfer; Reduction; ASYMMETRIC TRANSFER-HYDROGENATION; ENANTIOSELECTIVE REDUCTION; BORROWING HYDROGEN; KETONES; EFFICIENT; LIGANDS; COMPLEXES; ALCOHOLS; ALDEHYDES; DIAMINE;
D O I
10.1002/ejoc.201301020
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The ruthenium-catalyzed transfer hydrogenation of electron-rich amino-substituted acetophenones is reported. Variation of the reductant, ligands, base, and solvent allowed reaction optimization. A key discovery was the use of 1,4-butanediol as an irreversible reducing agent, which significantly improved the conversion. A range of amino- and amido-substituted aryl ketones were explored, and they all gave the corresponding alcohols in good yield, which demonstrates the wider applicability of this process.
引用
收藏
页码:6784 / 6788
页数:5
相关论文
共 50 条
  • [31] Boron Lewis Acid Promoted Ruthenium-Catalyzed Hydrogenation of Amides: An Efficient Approach to Secondary Amines
    Yuan, Ming-Lei
    Xie, Jian-Hua
    Zhou, Qi-Lin
    CHEMCATCHEM, 2016, 8 (19) : 3036 - 3040
  • [32] DIRECTING EFFECT OF FUNCTIONAL-GROUPS IN RUTHENIUM-CATALYZED ADDITION OF SUBSTITUTED ACETOPHENONES TO AN OLEFIN
    SONODA, M
    KAKIUCHI, F
    CHATANI, N
    MURAI, S
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1995, 504 (1-2) : 151 - 152
  • [33] Transfer Hydrogenation of Ketones, Nitriles, and Esters Catalyzed by a Half-Sandwich Complex of Ruthenium
    Lee, Sun-Hwa
    Nikonov, Georgii I.
    CHEMCATCHEM, 2015, 7 (01) : 107 - 113
  • [34] Ruthenium-Catalyzed Synthesis of Quinazolinones through Hydrogen Transfer and Cyclization
    Qiao, Jingyi
    Jiang, Hongshuo
    Liu, Xiaochong
    Xu, Chunzhao
    Sun, Zhizhong
    Chu, Wenyi
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2019, 2019 (13) : 2428 - 2434
  • [35] Ruthenium-Catalyzed Enantioselective Hydrogenation of Phenanthridine Derivatives
    Yang, Zhusheng
    Chen, Fei
    Zhang, Shuxin
    He, Yanmei
    Yang, Nianfa
    Fan, Qing-Hua
    ORGANIC LETTERS, 2017, 19 (06) : 1458 - 1461
  • [36] Ruthenium-catalyzed enantioselective hydrogenation of quinoxalinones and quinazolinones
    Li, Chenghao
    Zhang, Shuxin
    Li, Shan
    Feng, Yu
    Fan, Qing-Hua
    ORGANIC CHEMISTRY FRONTIERS, 2022, 9 (02): : 400 - 406
  • [37] Ruthenium-Catalyzed Transfer Hydrogenation of Nitriles: Reduction and Subsequent N-Monoalkylation to Secondary Amines
    Werkmeister, Svenja
    Bornschein, Christoph
    Junge, Kathrin
    Beller, Matthias
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2013 (18) : 3671 - 3674
  • [38] Proline-Derived Aminotriazole Ligands: Preparation and Use in the Ruthenium-Catalyzed Asymmetric Transfer Hydrogenation
    Cambeiro, Xacobe C.
    Pericas, Miquel A.
    ADVANCED SYNTHESIS & CATALYSIS, 2011, 353 (01) : 113 - 124
  • [39] Database Construction for the Virtual Screening of the Ruthenium-Catalyzed Hydrogenation of Ketones
    Nakajima, Haruno
    Murata, Chihaya
    Noto, Naoki
    Saito, Susumu
    JOURNAL OF ORGANIC CHEMISTRY, 2025, 90 (02) : 1054 - 1060
  • [40] Ruthenium-catalyzed transfer hydrogenation of imines by propan-2-ol in benzene
    Samec, JSM
    Bäckvall, JE
    CHEMISTRY-A EUROPEAN JOURNAL, 2002, 8 (13) : 2955 - 2961