Iridium catalyzed reversible dehydrogenation - Hydrogenation of quinoline derivatives under mild conditions

被引:68
作者
Manas, Michael G. [1 ]
Sharninghausen, Liam S. [1 ]
Lin, Elisa [1 ]
Crabtree, Robert H. [1 ]
机构
[1] Yale Univ, Dept Chem, New Haven, CT 06520 USA
关键词
Acceptorless dehydrogenation; Hydrogen storage; LOHCs; Heterocycles; ACCEPTORLESS DEHYDROGENATION; NITROGEN-HETEROCYCLES; N-HETEROCYCLES; STORAGE;
D O I
10.1016/j.jorganchem.2015.04.015
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
The potential of a hydrogen-based energy economy is limited by the fact that hydrogen gas is difficult to store and transport. Storing hydrogen in the form of liquid organic hydrogen-carriers (LOHCs) is a highly attractive alternative to current options but it requires the development of catalytic means of reversibly hydrogenating and dehydrogenating these carriers under mild conditions and ideally using a single catalyst for both processes. We report the optimization of two families of previously reported hydrogenation catalysts for the reverse reaction, dehydrogenation of N-heterocyclic substrates. These complexes are capable of catalyzing both dehydrogenation and hydrogenation reactions in alternation, giving high yields in both directions. Importantly, our complexes do not require high temperatures, high pressures of H-2 or strong base for the hydrogenation step. (C) 2015 Elsevier B.V. All rights reserved.
引用
收藏
页码:184 / 189
页数:6
相关论文
共 33 条
[1]  
[Anonymous], CHEM COMM
[2]   The Hydrogen Issue [J].
Armaroli, Nicola ;
Balzani, Vincenzo .
CHEMSUSCHEM, 2011, 4 (01) :21-36
[3]   Palladium-catalyzed asymmetric hydrogenation of 3-phthalimido substituted quinolines [J].
Cai, Xian-Feng ;
Huang, Wen-Xue ;
Chen, Zhang-Pei ;
Zhou, Yong-Gui .
CHEMICAL COMMUNICATIONS, 2014, 50 (67) :9588-9590
[4]   A Molecular Iron Catalyst for the Acceptorless Dehydrogenation and Hydrogenation of N-Heterocycles [J].
Chakraborty, Sumit ;
Brennessel, William W. ;
Jones, William D. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (24) :8564-8567
[5]   Computational structure-activity relationships in H2 storage:: how placement of N atoms affects release temperatures in organic liquid storage materials [J].
Clot, Eric ;
Eisenstein, Odile ;
Crabtree, Robert H. .
CHEMICAL COMMUNICATIONS, 2007, (22) :2231-2233
[6]   Hydrogen storage in liquid organic heterocycles [J].
Crabtree, Robert H. .
ENERGY & ENVIRONMENTAL SCIENCE, 2008, 1 (01) :134-138
[7]   The effect of substitution on the utility of piperidines and octahydroindoles for reversible hydrogen storage [J].
Cui, Yi ;
Kwok, Samantha ;
Bucholtz, Andrew ;
Davis, Boyd ;
Whitney, Ralph A. ;
Jessop, Philip G. .
NEW JOURNAL OF CHEMISTRY, 2008, 32 (06) :1027-1037
[8]   Highly selective hydrogenation of quinolines promoted by recyclable polymer supported palladium nanoparticles under mild conditions in aqueous medium [J].
Dell'Anna, Maria Michela ;
Capodiferro, Vito Filippo ;
Mali, Matilda ;
Manno, Daniela ;
Cotugno, Pietro ;
Monopoli, Antonio ;
Mastrorilli, Piero .
APPLIED CATALYSIS A-GENERAL, 2014, 481 :89-95
[9]   Iridium-Catalyzed Hydrogenation of N-Heterocyclic Compounds under Mild Conditions by an Outer-Sphere Pathway [J].
Dobereiner, Graham E. ;
Nova, Ainara ;
Schley, Nathan D. ;
Hazari, Nilay ;
Miller, Scott J. ;
Eisenstein, Odile ;
Crabtree, Robert H. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (19) :7547-7562
[10]   Chemical and Physical Solutions for Hydrogen Storage [J].
Eberle, Ulrich ;
Felderhoff, Michael ;
Schueth, Ferdi .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (36) :6608-6630