PDF herunterladen
Synlett 2011(18): 2643-2647  
DOI: 10.1055/s-0031-1289291
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

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

Samuel L. Bournea, Peter Koosa, Matthew O’Briena, Benjamin Martinb, Berthold Schenkelb, Ian R. Baxendalea, Steven V. Ley*a
a Innovative Technology Centre, Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge, CB2 1EW, UK
e-Mail: svl1000@cam.ac.uk;
b Chemical & Analytical Development, Novartis Pharma AG, Werk Klybeck, Klybeckstr. 141, 4057 Basel, Switzerland
Weitere Informationen

Publikationsverlauf

Received 19 August 2011
Publikationsdatum:
07. Oktober 2011 (online)

    Lizenzen und Reprints Alle Artikel dieser Rubrik

Abstract

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.

Key words

vinylation - membrane - flow - ethylene - styrene

    References and Notes

  • 1a Anastas PT. Kirchhoff MM. Acc. Chem. Res.  2002,  35:  686 
    Google Scholar
  • 1b Cavani F. Centi G. Perathoner S. Trifiro F. Sustainable Industrial Chemistry   Wiley-VCH; Weinheim: 2009. 
    Google Scholar
  • 1c Winterton N. Green Chemistry for Sustainable Technologies: A Foundation   RSC; Cambridge: 2010. 
    Google Scholar
  • 2a Trost BM. Angew. Chem., Int. Ed. Engl.  1995,  34:  259 
    Google Scholar
  • 2b Wender P. Acc. Chem. Res.  2008,  41:  40 
    Google Scholar
  • 2c Wender P. Organic Synthesis: Theory and Applications  1993,  2:  27 
    Google Scholar
  • 3a Webb D. Jamison TF. Chem. Sci.  2010,  1:  675 
    Google Scholar
  • 3b Hartman RL. Jensen KF. Lab Chip  2009,  9:  2495 
    Google Scholar
  • 3c Mason BP. Price KE. Steinbacher JL. Bogdan AR. McQuade DT. Chem. Rev.  2007,  107:  2300 
    Google Scholar
  • 3d Wegner J. Ceylan S. Kirschning A. Chem. Commun.  2011,  47:  4583 
    Google Scholar
  • 3e Wiles C. Watts P. Chem. Commun.  2011,  47:  6512 
    Google Scholar
  • 3f Baxendale IR. Hayward JJ. Lanners S. Ley SV. Smith CD. Microreactors in Organic Synthesis and Catalysis   Wirth T. Wiley; New York: 2008. 
    Google Scholar
  • 3g Kobayashi J. Mori Y. Okamoto K. Akiyama R. Ueno M. Kitamori T. Kobayashi S. Science  2004,  304:  1305 
    Google Scholar
  • 3h Yoshida JI. Chem. Rec.  2010,  10:  332 
    Google Scholar
  • 3i Mak XY. Laurino P. Seeberger PH. Beilstein J. Org. Chem.  2009,  5:  19 
    Google Scholar
  • 3j Razzaq T. Kappe CO. Chem. Asian J.  2010,  5:  1274 
    Google Scholar
  • 3k Hessel V. Chem. Eng. Technol.  2009,  32:  1655 
    Google Scholar
  • 3l Nieuwland PJ. Koch K. van Harskamp N. Wehrens R. van Hest JCM. Rutjes F. Chem. Asian J.  2010,  5:  799 
    Google Scholar
  • 3m Ahmed-Omer B. Brandt JC. Wirth T. Org. Biomol. Chem.  2007,  5:  733 
    Google Scholar
  • 3n Chambers RD. Fox MA. Sandford G. Trmcic J. Goeta A. J. Fluorine Chem.  2007,  128:  29 
    Google Scholar
  • 3o Fukuyama T. Rahman T. Kamata N. Ryu I. Beilstein J. Org. Chem.  2009,  5:  34 
    Google Scholar
  • 3p Miller PW. Jennings LE. deMello AJ. Gee AD. Long NJ. Vilar R. Adv. Synth. Catal.  2009,  351:  3260 
    Google Scholar
  • 3q Maurya RA. Park CP. Kim D.-P. Beilstein J. Org. Chem.  2011,  7:  1158 
    Google Scholar
  • 3r Park CP. Kim D.-P. J. Am. Chem. Soc.  2010,  132:  10102 
    Google Scholar
  • 4a Qian Z. Baxendale IR. Ley SV. Chem. Eur. J.  2010,  16:  12342 ; and references therein
    Google Scholar
  • 4b Hopkin MD. Baxendale IR. Ley SV. Chem. Commun.  2010,  46:  2450 
    Google Scholar
  • 5a Baxendale IR. Griffiths-Jones CM. Ley SV. Tranmer GK. Synlett  2006,  427 
    Google Scholar
  • 5b Brasholz M. Johnson BA. Macdonald JM. Polyzos A. Tsanaktsidis J. Saubern S. Holmes AB. Ryan JH. Tetrahedron  2010,  66:  6445 
    Google Scholar
  • 5c Baxendale IR. Deeley J. Griffiths-Jones CM. Ley SV. Saaby S. Tranmer GK. Chem. Commun.  2006,  2566 
    Google Scholar
  • 5d Hodgkinson JT. Galloway WRJD. Saraf S. Baxendale IR. Ley SV. Ladlow M. Welch M. Spring DR. Org. Biomol. Chem.  2011,  9:  57 
    Google Scholar
  • 5e Riva E. Rencurosi A. Gagliardi S. Passarella D. Martinelli M. Chem. Eur. J.  2011,  17:  6221 
    Google Scholar
  • 7a O’Brien M. Baxendale IR. Ley SV. Org. Lett.  2010,  12:  1596 
    Google Scholar
  • 7b Petersen TP. Polyzos A. O’Brien M. Baxendale IR. Ley SV. ChemSusChem  2011, DOI: 10.1002/cssc.201100339
    Google Scholar
  • 7c Polyzos A. O’Brien M. Petersen TP. Baxendale IR. Ley SV. Angew. Chem. Int. Ed.  2011,  50:  1190 
    Google Scholar
  • 7d Koos P. Gross U. Polyzos A. O’Brien M. Baxendale IR. Ley SV. Org. Biomol. Chem.  2011,  9:  6903 
    Google Scholar
  • 7e O’Brien M. Taylor N. Polyzos A. Baxendale IR. Ley SV. Chem. Sci.  2011,  2:  1250 
    Google Scholar
  • 8 Zeller K.-P. Kowallik M. Haiss P. Org. Biomol. Chem.  2005,  3:  3210 
    Google Scholar
  • 9 Rosenberg ML. Gupta NS. Wragg D. Tilset M. J. Org. Chem.  2011,  76:  2465 
    CrossrefGoogle Scholar
  • 10a Littke AF. Fu GC. J. Am. Chem. Soc.  2001,  123:  6989 
    Google Scholar
  • 10b Nikbin N. Ladlow M. Ley SV. Org. Proc. Res. Dev.  2007,  11:  458 
    Google Scholar
  • 11 Lazzaronia R. Settambolob R. Alagonac G. Ghioc C. Coord. Chem. Rev.  2010,  254:  696 
    CrossrefGoogle Scholar
  • 12 Mizoroki T. Mori K. Ozaki A. Bull. Chem. Soc. Jpn.  1971,  44:  581 
    Google Scholar
  • 13a Heck RF. Nolley JP. J. Org. Chem.  1972,  37:  2320 
    Google Scholar
  • 13b Heck RF. J. Am. Chem. Soc.  1969,  91:  6707 
    Google Scholar
  • 14a Smith CR. RajanBabu TV. Tetrahedron  2010,  66:  1102 
    Google Scholar
  • 14b Kormos CM. Leadbeater NE. J. Org. Chem.  2008,  73:  3854 
    Google Scholar
  • 15 Molander G. Brown AR. J. Org. Chem.  2006,  71:  9681 
    CrossrefPubMedGoogle Scholar
  • 16 Farina V. Kapadia S. Krishnan B. Wang C. Liebeskind LS. J. Org. Chem.  1994,  59:  5905 
    CrossrefGoogle Scholar
  • 17 Surry DS. Buchwald SL. Chem. Sci.  2011,  2:  27 
    CrossrefPubMedGoogle Scholar
  • 18 Jeffery T. Tetrahedron  1996,  52:  10113 
    Google Scholar
  • 19a Carter CF. Baxendale IR. O’Brien M. Pavey JBJ. Ley SV. Org. Biomol. Chem.  2009,  7:  4594 
    Google Scholar
  • 19b Carter CF. Lange H. Ley SV. Baxendale IR. Wittkamp B. Goode JG. Gaunt NL. Org. Process Res. Dev.  2010,  14:  393 
    Google Scholar
  • 20 Kasinathan S. Bourne SL. Tolstoy P. Koos P. O’Brien M. Bates RW. Baxendale IR. Ley SV. Synlett  2011,  2648 
    Artikel in Thieme ConnectGoogle Scholar
6

Purchased from Biogeneral Inc., 9925 Mesa Rim Road, San Diego, CA, USA. www.biogeneral.com