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

Samuel L. Bourne; Peter Koos; Matthew O’Brien; Benjamin Martin; Berthold Schenkel; Ian R. Baxendale; Steven V. Ley

doi:10.1055/s-0031-1289291

LETTER

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

Samuel L. Bourne^a, Peter Koos^a, Matthew O’Brien^a, Benjamin Martin^b, Berthold Schenkel^b, Ian R. Baxendale^a, 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

Abstract

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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

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<A NAME="RD27311ST-1A">1a</A> Anastas PT. Kirchhoff MM. Acc. Chem. Res. 2002, 35: 686

<A NAME="RD27311ST-1B">1b</A> Cavani F. Centi G. Perathoner S. Trifiro F. Sustainable Industrial Chemistry Wiley-VCH; Weinheim: 2009.

<A NAME="RD27311ST-1C">1c</A> Winterton N. Green Chemistry for Sustainable Technologies: A Foundation RSC; Cambridge: 2010.

<A NAME="RD27311ST-2A">2a</A> Trost BM. Angew. Chem., Int. Ed. Engl. 1995, 34: 259

<A NAME="RD27311ST-2B">2b</A> Wender P. Acc. Chem. Res. 2008, 41: 40

<A NAME="RD27311ST-2C">2c</A> Wender P. Organic Synthesis: Theory and Applications 1993, 2: 27

<A NAME="RD27311ST-3A">3a</A> Webb D. Jamison TF. Chem. Sci. 2010, 1: 675

<A NAME="RD27311ST-3B">3b</A> Hartman RL. Jensen KF. Lab Chip 2009, 9: 2495

<A NAME="RD27311ST-3C">3c</A> Mason BP. Price KE. Steinbacher JL. Bogdan AR. McQuade DT. Chem. Rev. 2007, 107: 2300

<A NAME="RD27311ST-3D">3d</A> Wegner J. Ceylan S. Kirschning A. Chem. Commun. 2011, 47: 4583

<A NAME="RD27311ST-3E">3e</A> Wiles C. Watts P. Chem. Commun. 2011, 47: 6512

<A NAME="RD27311ST-3F">3f</A> Baxendale IR. Hayward JJ. Lanners S. Ley SV. Smith CD. Microreactors in Organic Synthesis and Catalysis Wirth T. Wiley; New York: 2008.

<A NAME="RD27311ST-3G">3g</A> Kobayashi J. Mori Y. Okamoto K. Akiyama R. Ueno M. Kitamori T. Kobayashi S. Science 2004, 304: 1305

<A NAME="RD27311ST-3H">3h</A> Yoshida JI. Chem. Rec. 2010, 10: 332

<A NAME="RD27311ST-3I">3i</A> Mak XY. Laurino P. Seeberger PH. Beilstein J. Org. Chem. 2009, 5: 19

<A NAME="RD27311ST-3J">3j</A> Razzaq T. Kappe CO. Chem. Asian J. 2010, 5: 1274

<A NAME="RD27311ST-3K">3k</A> Hessel V. Chem. Eng. Technol. 2009, 32: 1655

<A NAME="RD27311ST-3L">3l</A> Nieuwland PJ. Koch K. van Harskamp N. Wehrens R. van Hest JCM. Rutjes F. Chem. Asian J. 2010, 5: 799

<A NAME="RD27311ST-3M">3m</A> Ahmed-Omer B. Brandt JC. Wirth T. Org. Biomol. Chem. 2007, 5: 733

<A NAME="RD27311ST-3N">3n</A> Chambers RD. Fox MA. Sandford G. Trmcic J. Goeta A. J. Fluorine Chem. 2007, 128: 29

<A NAME="RD27311ST-3O">3o</A> Fukuyama T. Rahman T. Kamata N. Ryu I. Beilstein J. Org. Chem. 2009, 5: 34

<A NAME="RD27311ST-3P">3p</A> Miller PW. Jennings LE. deMello AJ. Gee AD. Long NJ. Vilar R. Adv. Synth. Catal. 2009, 351: 3260

<A NAME="RD27311ST-3Q">3q</A> Maurya RA. Park CP. Kim D.-P. Beilstein J. Org. Chem. 2011, 7: 1158

<A NAME="RD27311ST-3R">3r</A> Park CP. Kim D.-P. J. Am. Chem. Soc. 2010, 132: 10102

<A NAME="RD27311ST-4A">4a</A> Qian Z. Baxendale IR. Ley SV. Chem. Eur. J. 2010, 16: 12342 ; and references therein

<A NAME="RD27311ST-4B">4b</A> Hopkin MD. Baxendale IR. Ley SV. Chem. Commun. 2010, 46: 2450

<A NAME="RD27311ST-5A">5a</A> Baxendale IR. Griffiths-Jones CM. Ley SV. Tranmer GK. Synlett 2006, 427

<A NAME="RD27311ST-5B">5b</A> Brasholz M. Johnson BA. Macdonald JM. Polyzos A. Tsanaktsidis J. Saubern S. Holmes AB. Ryan JH. Tetrahedron 2010, 66: 6445

<A NAME="RD27311ST-5C">5c</A> Baxendale IR. Deeley J. Griffiths-Jones CM. Ley SV. Saaby S. Tranmer GK. Chem. Commun. 2006, 2566

<A NAME="RD27311ST-5D">5d</A> Hodgkinson JT. Galloway WRJD. Saraf S. Baxendale IR. Ley SV. Ladlow M. Welch M. Spring DR. Org. Biomol. Chem. 2011, 9: 57

<A NAME="RD27311ST-5E">5e</A> Riva E. Rencurosi A. Gagliardi S. Passarella D. Martinelli M. Chem. Eur. J. 2011, 17: 6221

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<A NAME="RD27311ST-7A">7a</A> O’Brien M. Baxendale IR. Ley SV. Org. Lett. 2010, 12: 1596

<A NAME="RD27311ST-7B">7b</A> Petersen TP. Polyzos A. O’Brien M. Baxendale IR. Ley SV. ChemSusChem 2011, DOI: 10.1002/cssc.201100339

<A NAME="RD27311ST-7C">7c</A> Polyzos A. O’Brien M. Petersen TP. Baxendale IR. Ley SV. Angew. Chem. Int. Ed. 2011, 50: 1190

<A NAME="RD27311ST-7D">7d</A> Koos P. Gross U. Polyzos A. O’Brien M. Baxendale IR. Ley SV. Org. Biomol. Chem. 2011, 9: 6903

<A NAME="RD27311ST-7E">7e</A> O’Brien M. Taylor N. Polyzos A. Baxendale IR. Ley SV. Chem. Sci. 2011, 2: 1250

<A NAME="RD27311ST-8">8</A> Zeller K.-P. Kowallik M. Haiss P. Org. Biomol. Chem. 2005, 3: 3210

<A NAME="RD27311ST-9">9</A> Rosenberg ML. Gupta NS. Wragg D. Tilset M. J. Org. Chem. 2011, 76: 2465

<A NAME="RD27311ST-10A">10a</A> Littke AF. Fu GC. J. Am. Chem. Soc. 2001, 123: 6989

<A NAME="RD27311ST-10B">10b</A> Nikbin N. Ladlow M. Ley SV. Org. Proc. Res. Dev. 2007, 11: 458

<A NAME="RD27311ST-11">11</A> Lazzaronia R. Settambolob R. Alagonac G. Ghioc C. Coord. Chem. Rev. 2010, 254: 696

<A NAME="RD27311ST-12">12</A> Mizoroki T. Mori K. Ozaki A. Bull. Chem. Soc. Jpn. 1971, 44: 581

<A NAME="RD27311ST-13A">13a</A> Heck RF. Nolley JP. J. Org. Chem. 1972, 37: 2320

<A NAME="RD27311ST-13B">13b</A> Heck RF. J. Am. Chem. Soc. 1969, 91: 6707

<A NAME="RD27311ST-14A">14a</A> Smith CR. RajanBabu TV. Tetrahedron 2010, 66: 1102

<A NAME="RD27311ST-14B">14b</A> Kormos CM. Leadbeater NE. J. Org. Chem. 2008, 73: 3854

<A NAME="RD27311ST-15">15</A> Molander G. Brown AR. J. Org. Chem. 2006, 71: 9681

<A NAME="RD27311ST-16">16</A> Farina V. Kapadia S. Krishnan B. Wang C. Liebeskind LS. J. Org. Chem. 1994, 59: 5905

<A NAME="RD27311ST-17">17</A> Surry DS. Buchwald SL. Chem. Sci. 2011, 2: 27

<A NAME="RD27311ST-18">18</A> Jeffery T. Tetrahedron 1996, 52: 10113

<A NAME="RD27311ST-19A">19a</A> Carter CF. Baxendale IR. O’Brien M. Pavey JBJ. Ley SV. Org. Biomol. Chem. 2009, 7: 4594

<A NAME="RD27311ST-19B">19b</A> Carter CF. Lange H. Ley SV. Baxendale IR. Wittkamp B. Goode JG. Gaunt NL. Org. Process Res. Dev. 2010, 14: 393

<A NAME="RD27311ST-20">20</A> Kasinathan S. Bourne SL. Tolstoy P. Koos P. O’Brien M. Bates RW. Baxendale IR. Ley SV. Synlett 2011, 2648