Reductive N-Alkylation of Nitro Compounds to N-Alkyl and N,N-Dialkyl Amines with Glycerol as the Hydrogen Source

被引:66
作者
Cui, Xinjiang [1 ,2 ,3 ]
Deng, Youquan [1 ]
Shi, Feng [1 ]
机构
[1] Chinese Acad Sci, Lanzhou Inst Chem Phys, Ctr Green Chem & Catalysis, Lanzhou 730000, Peoples R China
[2] Lanzhou Univ, State Key Lab Appl Organ Chem, Lanzhou 730000, Peoples R China
[3] Lanzhou Univ, Dept Chem, Lanzhou 730000, Peoples R China
来源
ACS CATALYSIS | 2013年 / 3卷 / 05期
关键词
amines; alcohols; N-alkylation; glycerol; renewable; catalysis; INTRAMOLECULAR HYDROAMINATION; SELECTIVE SYNTHESIS; SECONDARY ALCOHOLS; AMIDE SYNTHESIS; ARYL HALIDES; RUTHENIUM; EFFICIENT; SULFONAMIDES; NITROARENES; CATALYST;
D O I
10.1021/cs400049b
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
As the sustainable and promising hydrogen source, here glycerol was directly used as the hydrogen source for the reductive amination of alcohol using nitrobenzene as the starting material. The amination of alcohols, especially aliphatic alcohols with different structures, was realized, and mono- or disubstituted amines were synthesized with excellent yields. The reaction mechanism was also explored
引用
收藏
页码:808 / 811
页数:4
相关论文
共 55 条
[1]   Amines made easily: A highly selective hydroaminomethylation of olefins [J].
Ahmed, M ;
Seayad, AM ;
Jackstell, R ;
Beller, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (34) :10311-10318
[2]  
[Anonymous], 2005, BIOMASS FEEDSTOCK BI
[3]   Impregnated Ruthenium on Magnetite as a Recyclable Catalyst for the N-Alkylation of Amines, Sulfonamides, Sulfinamides, and Nitroarenes Using Alcohols as Electrophiles by a Hydrogen Autotransfer Process [J].
Cano, Rafael ;
Ramon, Diego J. ;
Yus, Miguel .
JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (14) :5547-5557
[4]   Semiconductor-based Photocatalytic Hydrogen Generation [J].
Chen, Xiaobo ;
Shen, Shaohua ;
Guo, Liejin ;
Mao, Samuel S. .
CHEMICAL REVIEWS, 2010, 110 (11) :6503-6570
[5]   Catalytic features of Rh and Ni supported catalysts in the steam reforming of glycerol to produce hydrogen [J].
Chiodo, V. ;
Freni, S. ;
Galvagno, A. ;
Mondello, N. ;
Frusteri, F. .
APPLIED CATALYSIS A-GENERAL, 2010, 381 (1-2) :1-7
[6]   A Bifunctional Pd/MgO Solid Catalyst for the One-Pot Selective N-Monoalkylation of Amines with Alcohols [J].
Corma, Avelino ;
Rodenas, Tania ;
Sabater, Maria J. .
CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (01) :254-260
[7]   Ruthenium-Catalyzed Nitro and Nitrile Compounds Coupling with Alcohols: Alternative Route for N-Substituted Amine Synthesis [J].
Cui, Xinjiang ;
Zhang, Yan ;
Shi, Feng ;
Deng, Youquan .
CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (09) :2587-2591
[8]   Organic Ligand-Free Alkylation of Amines, Carboxamides, Sulfonamides, and Ketones by Using Alcohols Catalyzed by Heterogeneous Ag/Mo Oxides [J].
Cui, Xinjiang ;
Zhang, Yan ;
Shi, Feng ;
Deng, Youquan .
CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (03) :1021-1028
[9]   Copper-Catalyzed N-Alkylation of Sulfonamides with Benzylic Alcohols: Catalysis and Mechanistic Studies [J].
Cui, Xinjiang ;
Shi, Feng ;
Tse, Man Kin ;
Goerdes, Dirk ;
Thurow, Kerstin ;
Beller, Matthias ;
Deng, Youquan .
ADVANCED SYNTHESIS & CATALYSIS, 2009, 351 (17) :2949-2958
[10]   Amide Synthesis from Alcohols and Amines Catalyzed by Ruthenium N-Heterocyclic Carbene Complexes [J].
Dam, Johan Hygum ;
Osztrovszky, Gyorgyi ;
Nordstrom, Lars Ulrik ;
Madsen, Robert .
CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (23) :6820-6827