Efficient Catalytic Hydrogenation of N-Unsubstituted Cyclic Imides to Cyclic Amines

被引：20

作者：

Maj, Anna M. ^{[1
]}

Suisse, Isabelle ^{[1
]}

Pinault, Nathalie ^{[2
]}

Robert, Nicolas ^{[2
]}

Agbossou-Niedercorn, Francine ^{[1
]}

机构：

[1] Univ Lille Nord France, CNRS, UCCS, BP 90108, F-59652 Villeneuve Dascq, France

[2] Oril Ind, F-76210 Bolbec, France

来源：

CHEMCATCHEM | 2014年 / 6卷 / 09期

关键词：

cyclic imides; heterogeneous catalysis; hydrogenation; molybdenum; rhodium; ENANTIOSELECTIVE HYDROGENATION; SELECTIVE HYDROGENATION; ACID DERIVATIVES; AMIDES; ESTERS; RUTHENIUM; ALCOHOLS; REDUCTION; COMPLEXES; DESYMMETRIZATION;

D O I：

10.1002/cctc.201402233

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：

The hydrogenation of N-unsubstituted cyclic imides to the corresponding cyclic amines has been performed selectively with heterogeneous catalysts obtained from rhodium and molybdenum carbonyl precursors. Various substrates were reduced in good to high yields and selectivities. Platinum-based catalysts also proved to be efficient. Furthermore, gram-scale experiments were performed and the catalysts could be recycled.

引用

页码：2621 / 2625

页数：5

共 66 条

[1] Homogeneous catalytic hydrogenation of long-chain esters by an osmium pincer complex and its potential application in the direct conversion of triglycerides into fatty alcohols [J].

Acosta-Ramirez, Alberto ;

Bertoli, Marcello ;

Gusev, Dmitry G. ;

Schlaf, Marcel .

GREEN CHEMISTRY, 2012, 14 (04) :1178-1188

[2] Selective Reduction of Carboxylic Acid Derivatives by Catalytic Hydrosilylation [J].

Addis, Daniele ;

Das, Shoubhik ;

Junge, Kathrin ;

Beller, Matthias .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (27) :6004-6011

[3] Chiral aminophosphine phosphinite ligands and related auxiliaries - Recent advances in their design, coordination chemistry, and use in enantioselective catalysis [J].

Agbossou-Niedercorn, F ;

Suisse, I .

COORDINATION CHEMISTRY REVIEWS, 2003, 242 (1-2) :145-158

[4] Concomitant monoreduction and hydrogenation of unsaturated cyclic imides to lactams catalyzed by ruthenium compounds [J].

Aoun, R ;

Renaud, JL ;

Dixneuf, PH ;

Bruneau, C .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (13) :2021-2023

[5]

Aoun R, 2003, [No title captured], Patent No. [FR 20030011226, 20030011226]

[6] Efficient hydrogenation of biomass-derived cyclic di-esters to 1,2-diols [J].

Balaraman, Ekambaram ;

Fogler, Eran ;

Milstein, David .

CHEMICAL COMMUNICATIONS, 2012, 48 (08) :1111-1113

[7] 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

[8] 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

[9] 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

[10] 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

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