The Continuous-Flow Synthesis of Styrenes Using Ethylene in a Palladium-Catalysed Heck Cross-Coupling Reaction

被引:58
作者
Bourne, Samuel L. [1 ]
Koos, Peter [1 ]
O'Brien, Matthew [1 ]
Martin, Benjamin [2 ]
Schenkel, Berthold [2 ]
Baxendale, Ian R. [1 ]
Ley, Steven V. [1 ]
机构
[1] Univ Cambridge, Dept Chem, Innovat Technol Ctr, Cambridge CB2 1EW, England
[2] Novartis Pharma AG, Chem & Analyt Dev, CH-4057 Basel, Switzerland
基金
英国工程与自然科学研究理事会;
关键词
vinylation; membrane; flow; ethylene; styrene; ORGANIC-SYNTHESIS; MICROREACTOR; CHEMISTRY; ARYL; ARYLATION; ECONOMY; HALIDES;
D O I
10.1055/s-0031-1289291
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
We report a palladium-catalysed ethylene Heck reaction for the vinylation of aryl iodides using a tube-in-tube gas-liquid reactor. The flow process afforded various styrenes in short reaction times, employing moderate ethylene pressure.
引用
收藏
页码:2643 / 2647
页数:5
相关论文
共 53 条
[1]   Advanced organic synthesis using microreactor technology [J].
Ahmed-Omer, Batoul ;
Brandt, Johan C. ;
Wirth, Thomas .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2007, 5 (05) :733-740
[2]   Origins, current status, and future challenges of green chemistry [J].
Anastas, PT ;
Kirchhoff, MM .
ACCOUNTS OF CHEMICAL RESEARCH, 2002, 35 (09) :686-694
[3]  
Baxendale I. R., 2008, MICROREACTORS ORGANI
[4]   A flow process for the multi-step synthesis of the alkaloid natural product oxomaritidine: a new paradigm for molecular assembly [J].
Baxendale, Ian R. ;
Deeley, Jon ;
Griffiths-Jones, Charlotte M. ;
Ley, Steven V. ;
Saaby, Steen ;
Tranmer, Geoffrey K. .
CHEMICAL COMMUNICATIONS, 2006, (24) :2566-2568
[5]   Preparation of the neolignan natural product grossamide by a continuous-flow process [J].
Baxendale, IR ;
Griffiths-Jones, CM ;
Ley, SV ;
Tranmer, GK .
SYNLETT, 2006, (03) :427-430
[6]   Flow synthesis of tricyclic spiropiperidines as building blocks for the histrionicotoxin family of alkaloids [J].
Brasholz, Malte ;
Johnson, Brian A. ;
Macdonald, James M. ;
Polyzos, Anastasios ;
Tsanaktsidis, John ;
Saubern, Simon ;
Holmes, Andrew B. ;
Ryan, John H. .
TETRAHEDRON, 2010, 66 (33) :6445-6449
[7]   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
[8]   Synthesis of acetal protected building blocks using flow chemistry with flow IR analysis: preparation of butane-2,3-diacetal tartrates [J].
Carter, Catherine F. ;
Baxendale, Ian R. ;
O'Brien, Matthew ;
Pavey, John B. J. ;
Ley, Steven V. .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2009, 7 (22) :4594-4597
[9]  
Cavani F., 2009, Sustainable industrial chemistry: Principles, tools and industrial examples
[10]   Elemental fluorine - Part 20. Direct fluorination of deactivated aromatic systems using microreactor techniques [J].
Chambers, Richard D. ;
Fox, Mark A. ;
Sandford, Graham ;
Trmcic, Jelena ;
Goeta, Andres .
JOURNAL OF FLUORINE CHEMISTRY, 2007, 128 (01) :29-33