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
    Ahmed-Omer, Batoul
    Brandt, Johan C.
    Wirth, Thomas
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2007, 5 (05) : 733 - 740
  • [2] Origins, current status, and future challenges of green chemistry
    Anastas, PT
    Kirchhoff, MM
    [J]. 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
    Baxendale, Ian R.
    Deeley, Jon
    Griffiths-Jones, Charlotte M.
    Ley, Steven V.
    Saaby, Steen
    Tranmer, Geoffrey K.
    [J]. CHEMICAL COMMUNICATIONS, 2006, (24) : 2566 - 2568
  • [5] Preparation of the neolignan natural product grossamide by a continuous-flow process
    Baxendale, IR
    Griffiths-Jones, CM
    Ley, SV
    Tranmer, GK
    [J]. SYNLETT, 2006, (03) : 427 - 430
  • [6] Flow synthesis of tricyclic spiropiperidines as building blocks for the histrionicotoxin family of alkaloids
    Brasholz, Malte
    Johnson, Brian A.
    Macdonald, James M.
    Polyzos, Anastasios
    Tsanaktsidis, John
    Saubern, Simon
    Holmes, Andrew B.
    Ryan, John H.
    [J]. TETRAHEDRON, 2010, 66 (33) : 6445 - 6449
  • [7] ReactIR Flow Cell: A New Analytical Tool for Continuous Flow Chemical Processing
    Carter, Catherine F.
    Lange, Heiko
    Ley, Steven V.
    Baxendale, Ian R.
    Wittkamp, Brian
    Goode, Jon G.
    Gaunt, Nigel L.
    [J]. 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
    Carter, Catherine F.
    Baxendale, Ian R.
    O'Brien, Matthew
    Pavey, John B. J.
    Ley, Steven V.
    [J]. 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
    Chambers, Richard D.
    Fox, Mark A.
    Sandford, Graham
    Trmcic, Jelena
    Goeta, Andres
    [J]. JOURNAL OF FLUORINE CHEMISTRY, 2007, 128 (01) : 29 - 33