Asymmetric Homogeneous Hydrogenation in Flow using a Tube-in-Tube Reactor

被引:68
作者
Newton, Sean [1 ]
Ley, Steven V. [1 ]
Arce, Eva Casas [2 ]
Grainger, Damian M. [2 ]
机构
[1] Univ Cambridge, Dept Chem, Cambridge CB2 1EW, England
[2] Cambridge Sci Pk, Johnson Matthey Catalysis & Chiral Technol, Unit 28, Cambridge CB4 0FP, England
基金
英国工程与自然科学研究理事会;
关键词
asymmetric catalysis; homogeneous catalysis; hydrogenation; iridium; microreactors; rhodium; CATALYZED ENANTIOSELECTIVE HYDROGENATION; PHOSPHINITE-OXAZOLINE LIGANDS; OPPORTUNITIES NOBEL LECTURE; ORGANIC-SYNTHESIS; CHANGING FACE; IRIDIUM; ALKENES; OLEFINS; SOLUBILITY; COMPLEXES;
D O I
10.1002/adsc.201200073
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
In this update, the asymmetric homogeneous hydrogenation of a number of trisubstituted olefins utilizing the recently developed tube-in-tube gas-liquid flow reactor is described. A number of chiral iridium- and rhodium-based catalysts and other parameters such as pressure, solvent, temperature and catalyst loading were screened. The advantage of the flow set-up for rapid screening and optimization of reaction parameters is illustrated. Furthermore, a comparative study using batch conditions aided in the optimization of the flow reaction set-up. The set-up was further modified to recycle the catalyst which prolonged catalytic activity.
引用
收藏
页码:1805 / 1812
页数:8
相关论文
共 62 条
[1]  
Baxendale I. R., 2006, ERNST SCHER FDN S P, P151
[2]  
Blankenstein J, 2001, ANGEW CHEM INT EDIT, V40, P4445, DOI 10.1002/1521-3773(20011203)40:23<4445::AID-ANIE4445>3.0.CO
[3]  
2-V
[4]  
Blankenstein J., 2001, Angew. Chem, V113, P4577
[5]   Phosphinoferrocenylaminophosphines as novel and practical ligands for asymmetric catalysis [J].
Boaz, NW ;
Debenham, SD ;
Mackenzie, EB ;
Large, SE .
ORGANIC LETTERS, 2002, 4 (14) :2421-2424
[6]   The Continuous-Flow Synthesis of Styrenes Using Ethylene in a Palladium-Catalysed Heck Cross-Coupling Reaction [J].
Bourne, Samuel L. ;
Koos, Peter ;
O'Brien, Matthew ;
Martin, Benjamin ;
Schenkel, Berthold ;
Baxendale, Ian R. ;
Ley, Steven V. .
SYNLETT, 2011, (18) :2643-2647
[7]  
BROWN JM, 1999, COMPREHENSIVE ASYMME, V1, P1
[8]   SOLUBILITY OF HYDROGEN IN 10 ORGANIC-SOLVENTS AT 298.15-K, 323.15-K, AND 373.15-K [J].
BRUNNER, E .
JOURNAL OF CHEMICAL AND ENGINEERING DATA, 1985, 30 (03) :269-273
[9]   ReactIR Flow Cell: A New Analytical Tool for Continuous Flow Chemical Processing [J].
Carter, Catherine F. ;
Lange, Heiko ;
Ley, Steven V. ;
Baxendale, Ian R. ;
Wittkamp, Brian ;
Goode, Jon G. ;
Gaunt, Nigel L. .
ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2010, 14 (02) :393-404
[10]   IRIDIUM COMPOUNDS IN CATALYSIS [J].
CRABTREE, R .
ACCOUNTS OF CHEMICAL RESEARCH, 1979, 12 (09) :331-338