Silver-Catalyzed Biomimetic Transfer Hydrogenation of N-Heteroaromatics with Hantzsch Esters as NADH Analogues

被引:14
|
作者
Pi, Danwei [1 ]
Zhou, Haifeng [1 ]
Cui, Peng [1 ]
He, Renke [1 ]
Sui, Yuebo [1 ]
机构
[1] China Three Gorges Univ, Coll Biol & Pharmaceut Sci, Hubei Key Lab Nat Prod Res & Dev, Yichang 443002, Peoples R China
来源
CHEMISTRYSELECT | 2017年 / 2卷 / 13期
基金
中国国家自然科学基金;
关键词
Hantzsch ester; N-heteroaromatics; silver catalysis; transfer hydrogenation; ASYMMETRIC TRANSFER HYDROGENATION; ENANTIOSELECTIVE PROPARGYLATION REACTIONS; TEMPERATURE CO OXIDATION; BRONSTED ACID; CYCLOADDITION REACTIONS; CARBONYL-COMPOUNDS; ETHYLENE OXIDE; REDUCTION; QUINOLINES; DEHYDROGENATION;
D O I
10.1002/slct.201700327
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A silver-catalyzed biomimetic transfer hydrogenation of Nheteroaromatics with Hantzsch esters as NADH analogues has been developed. The reaction proceeded smoothly under mild conditions to give the corresponding reductive products in up to 99% yield. The asymmetric version of this reaction was also conducted preliminarily with up to 66% ee.
引用
收藏
页码:3976 / 3979
页数:4
相关论文
共 17 条
  • [1] Copper-Catalyzed Transfer Hydrogenation of N-Heteroaromatics with an Oxazaborolidine Complex
    Zhong, Yuanhai
    Zhou, Taigang
    Zhang, Zhuohua
    Chang, Ruiqing
    ACS OMEGA, 2019, 4 (05): : 8487 - 8494
  • [2] Recent developments in asymmetric transfer hydrogenation with Hantzsch esters: A biomimetic approach
    You, Shu-Li
    CHEMISTRY-AN ASIAN JOURNAL, 2007, 2 (07) : 820 - 827
  • [3] Diboron-Assisted Palladium-Catalyzed Transfer Hydrogenation of N-Heteroaromatics with Water as Hydrogen Donor and Solvent
    Xuan, Qingqing
    Song, Qiuling
    ORGANIC LETTERS, 2016, 18 (17) : 4250 - 4253
  • [4] A silver-catalyzed transfer hydrogenation of aldehyde in air and water
    Liu, Mingxin
    Zhou, Feng
    Jia, Zhenhua
    Li, Chao-Jun
    ORGANIC CHEMISTRY FRONTIERS, 2014, 1 (02): : 161 - 166
  • [5] Enantioselective hydrogenation of N-heteroaromatics catalyzed by chiral diphosphine modified binaphthyl palladium nanoparticles
    Xia, Yun-Tao
    Ma, Jing
    Wang, Xiao-Dong
    Yang, Lei
    Wu, Lei
    CATALYSIS SCIENCE & TECHNOLOGY, 2017, 7 (23) : 5515 - 5520
  • [6] Iridium-catalyzed asymmetric transfer hydrogenation of quinolines with Hantzsch esters
    Wang, Da-Wei
    Zeng, Wei
    Zhou, Yong-Gui
    TETRAHEDRON-ASYMMETRY, 2007, 18 (09) : 1103 - 1107
  • [7] Silver-Catalyzed Functionalization of Esters by Carbene Transfer: The Role of Ylide Zwitterionic Intermediates
    Gava, Riccardo
    Angeles Fuentes, M.
    Besora, Maria
    Belderrain, Tomas R.
    Jacob, Kane
    Maseras, Feliu
    Etienne, Michel
    Caballero, Ana
    Perez, Pedro J.
    CHEMCATCHEM, 2014, 6 (08) : 2206 - 2210
  • [8] 4CzIPN-tBu-Catalyzed Proton-Coupled Electron Transfer for Photosynthesis of Phosphorylated N-Heteroaromatics
    Liu, Yan
    Chen, Xiao-Lan
    Li, Xiao-Yun
    Zhu, Shan-Shan
    Li, Shi-Jun
    Song, Yan
    Qu, Ling-Bo
    Yu, Bing
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2021, 143 (02) : 964 - 972
  • [9] ELECTRON-TRANSFER PROCESSES - MECHANISMS OF OXIDATION OF ETHERS AND ESTERS BY SILVER-CATALYZED PEROXYDISULFATE
    MINISCI, F
    COPPA, F
    FONTANA, F
    ZHAO, LH
    GAZZETTA CHIMICA ITALIANA, 1993, 123 (11): : 613 - 616
  • [10] Silver-Catalyzed Enantioselective Mannich Reaction of Diazoacetate Esters with N-Boc Aldimines
    Robertson, Gerard P.
    Farley, Alistair J. M.
    Dixon, Darren J.
    JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (04): : 2785 - 2792