Lewis Acid-Promoted Heterogeneous Platinum Catalysts for Hydrogenation of Amides to Amines

被引：46
作者：
Shimizu, Ken-ichi [1 ,2 ]
Onodera, Wataru [1 ]
Touchy, Abeda S. [1 ]
Siddiki, S. M. A. H. [2 ]
Toyao, Takashi [1 ,2 ]
Kon, Kenichi [1 ]
机构：
[1] Hokkaido Univ, Inst Catalysis, N-21,W-10, Sapporo, Hokkaido, Japan
[2] Kyoto Univ, Elements Strategy Initiat Catalysis & Batteries, Kyoto 6158520, Japan
来源：
CHEMISTRYSELECT | 2016年 / 1卷 / 04期
关键词：
amide hydrogenation; amines; Lewis acids; heterogeneous catalysis; platinum; SELECTIVE HYDROGENATION; ALCOHOLS; COMPLEX; SYSTEM;
D O I：
10.1002/slct.201600088
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
For the hydrogenation of a tertiary amide (N-acetylpiperidine), Lewis acidic support materials (Nb2O5 and MoOx/TiO2) increase the catalytic activity of Pt metal nanoparticles by a factor of > 100. In situ infrared (IR) study shows that coordination of the C=O group of amide to surface Lewis acid sites weakens the C=O bond, and the activated amide undergoes hydrogen transfer from H species on Pt sites. Among 19 types of heterogeneous catalysts tested, Pt/Nb2O5 shows the highest catalytic activity. Pt/Nb2O5 is generally effective for the selective hydrogenation of various tertiary amides and e-caprolactam to the corresponding amines under additive-free and solventless conditions and shows an order of higher turnover number (TON) than previously reported catalysts. Pt-MoOx/TiO2 is the secondary most effective and is reusable 10 times after the reaction.
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收藏
页码：736 / 740
页数：5
相关论文
共 33 条
[1]   Direct Hydrogenation of Amides to Alcohols and Amines under Mild Conditions [J].
Balaraman, Ekambaram ;
Gnanaprakasam, Boopathy ;
Shimon, Linda J. W. ;
Milstein, David .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (47) :16756-16758
[2]   Selective hydrogenation of amides using bimetallic Ru/Re and Rh/Re catalysts [J].
Beamson, Graham ;
Papworth, Adam J. ;
Philipps, Charles ;
Smith, Andrew M. ;
Whyman, Robin .
JOURNAL OF CATALYSIS, 2011, 278 (02) :228-238
[3]   Selective Hydrogenation of Amides using Ruthenium/Molybdenum Catalysts [J].
Beamson, Graham ;
Papworth, Adam J. ;
Philipps, Charles ;
Smith, Andrew M. ;
Whyman, Robin .
ADVANCED SYNTHESIS & CATALYSIS, 2010, 352 (05) :869-883
[4]   Selective hydrogenation of amides using Rh/Mo catalysts [J].
Beamson, Graham ;
Papworth, Adam J. ;
Philipps, Charles ;
Smith, Andrew M. ;
Whyman, Robin .
JOURNAL OF CATALYSIS, 2010, 269 (01) :93-102
[5]   PROMOTION OF CO AND CO2 HYDROGENATION OVER RH BY METAL-OXIDES - THE INFLUENCE OF OXIDE LEWIS ACIDITY AND REDUCIBILITY [J].
BOFFA, A ;
LIN, C ;
BELL, AT ;
SOMORJAI, GA .
JOURNAL OF CATALYSIS, 1994, 149 (01) :149-158
[6]   Catalytic hydrogenation of tertiary amides at low temperatures and pressures using bimetallic Pt/Re-based catalysts [J].
Burch, R. ;
Paun, C. ;
Cao, X. -M. ;
Crawford, P. ;
Goodrich, P. ;
Hardacre, C. ;
Hu, P. ;
McLaughlin, L. ;
Sa, J. ;
Thompson, J. M. .
JOURNAL OF CATALYSIS, 2011, 283 (01) :89-97
[7]   Efficient Base-Free Hydrogenation of Amides to Alcohols and Amines Catalyzed by Well-Defined Pincer Imidazolyl-Ruthenium Complexes [J].
Cabrero-Antonino, Jose R. ;
Alberico, Elisabetta ;
Drexler, Hans-Joachim ;
Baumann, Wolfgang ;
Junge, Kathrin ;
Junge, Henrik ;
Beller, Matthias .
ACS CATALYSIS, 2016, 6 (01) :47-54
[8]   Density Functional Theory Study on the Cleavage Mechanism of the Carbonyl Bond in Amides on Flat and Stepped Ru Surfaces: Hydrogen-Induced or Direct C-O Bond Breaking? [J].
Cao, Xiao-Ming ;
Burch, Robbie ;
Hardacre, Christopher ;
Hu, P. .
JOURNAL OF PHYSICAL CHEMISTRY C, 2012, 116 (35) :18713-18721
[9]   The First Continuous Flow Hydrogenation of Amides to Amines [J].
Coetzee, Jacorien ;
Manyar, Haresh G. ;
Hardacre, Christopher ;
Cole-Hamilton, David J. .
CHEMCATCHEM, 2013, 5 (10) :2843-2847
[10]   Homogeneous Catalytic Hydrogenation of Amides to Amines [J].
Coetzee, Jacorien ;
Dodds, Deborah L. ;
Klankermayer, Juergen ;
Brosinski, Sandra ;
Leitner, Walter ;
Slawin, Alexandra M. Z. ;
Cole-Hamilton, David J. .
CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (33) :11039-11050
1234