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Synthesis 2012(1): 37-41  
DOI: 10.1055/s-0031-1289585
PSP
© Georg Thieme Verlag Stuttgart ˙ New York

A Sustainable Procedure Combining the Advantages of Both Homogeneous and Heterogeneous Catalysis for the Heck-Matsuda Reaction

Cybille Rossya, Eric Fouqueta, François-Xavier Felpin*a,b
a Université de Bordeaux, CNRS-UMR 5255, Institut des Sciences Moléculaires, 351 cours de la Libération, 33405 Talence, France
b Université de Nantes, UFR Sciences et Techniques, UMR CNRS 6230, CEISAM, 2 rue de la Houssinière, BP 92208, 44322 Nantes Cedex 3, France
Fax: +33(25)1125402; e-Mail: fx.felpin@univ-nantes.fr;
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Publikationsverlauf

Received 9 September 2011
Publikationsdatum:
03. November 2011 (online)

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Abstract

A sustainable procedure has been introduced for the Heck-Matsuda reaction between arenediazonium salts and olefins. Our approach advantageously combines the high reactivity attained in homogeneous catalysis with the recovery of palladium metal by simple filtration usually encountered in heterogeneous catalysis. To reach such a useful catalytic system, a homogeneous source of palladium, Pd(OAc)2, reduced into a catalytically active soluble palladium species, was used in the presence of charcoal and deposited progressively onto the support when it became inactive. Measurement of palladium content shows only a low contamination of the solvent and the product after simple filtration.

Key words

palladium - heterogeneous catalysis - homogeneous catalysis - charcoal - Heck-Matsuda Reaction

    References

  • For reviews, see:
  • 1a Roglans A. Pla-Quintana A. Moreno-Mañas M. Chem. Rev.  2006,  106:  4622 
    Google Scholar
  • 1b Taylor JG. Venturini Moro A. Correia RCD. Eur. J. Org. Chem.  2011,  1403 
    Google Scholar
  • 1c Felpin F.-X. Nassar-Hardy L. Le Callonnec F. Fouquet E. Tetrahedron  2011,  67:  2815 
    Google Scholar
  • For selected recent examples, see:
  • 2a Darses S. Pucheault M. Genêt J.-P. Eur. J. Org. Chem.  2001,  1121 
    Google Scholar
  • 2b Andrus MB. Song C. Zhang J. Org. Lett.  2002,  4:  2079 
    Google Scholar
  • 2c Selvakumar K. Zapf A. Spannenberg A. Beller M. Chem. Eur. J.  2002,  8:  3901 
    Google Scholar
  • 2d Masllorens J. Moreno-Mañas M. Pla-Quintana A. Roglans A. Org. Lett.  2003,  5:  1559 
    Google Scholar
  • 2e Schmidt B. Chem. Commun.  2003,  1656 
    Google Scholar
  • 2f Severino EA. Costenaro ER. Garcia ALL. Correia CRD. Org. Lett.  2003,  5:  305 
    Google Scholar
  • 2g Masllorens J. Bouquillon S. Roglans A. Hénin F. Muzart J. J. Organomet. Chem.  2005,  690:  3822 
    Google Scholar
  • 2h Pla-Quintana A. Roglans A. ARKIVOC  2005,  (ix):  51 
    Google Scholar
  • 2i Artuso E. Barbero M. Degani I. Dughera S. Fochi R. Tetrahedron  2006,  62:  3146 
    Google Scholar
  • 2j Barbero M. Cadamuro S. Dughera S. Synthesis  2006,  3443 
    Google Scholar
  • 2k Pastre JC. Duarte Correia CR. Org. Lett.  2006,  8:  1657 
    Google Scholar
  • 2l Schmidt B. Biernat A. Eur. J. Org. Chem.  2008,  5764 
    Google Scholar
  • 2m Cacchi S. Fabrizi G. Goggiamani A. Sferrazza A. Synlett  2009,  1277 
    Google Scholar
  • 2n Schmidt B. Hölter F. Chem. Eur. J.  2009,  15:  11948 
    Google Scholar
  • 2o Coy BED. Jovanovic L. Sefkow M. Org. Lett.  2010,  12:  1976 
    Google Scholar
  • 2p Schmidt B. Berger R. Holter F. Org. Biomol. Chem.  2010,  8:  1406 
    Google Scholar
  • 2q Schmidt B. Hölter F. Berger R. Jessel S. Adv. Synth. Catal.  2010,  352:  2463 
    Google Scholar
  • 2r Stern T. Rückbrod S. Czekelius C. Donner C. Brunner H. Adv. Synth. Catal.  2010,  352:  1983 
    Google Scholar
  • 2s Schmidt B. Hölter F. Kelling A. Schilde U. J. Org. Chem.  2011,  76:  3357 
    Google Scholar
  • 2t Taylor JG. Correia CRD. J. Org. Chem.  2011,  76:  857 
    Google Scholar
  • 2u Kalkhambkar RG. Laali KK. Tetrahedron Lett.  2011,  52:  1733 
    Google Scholar
  • 3 Felpin F.-X. Fouquet E. Zakri C. Adv. Synth. Catal.  2008,  350:  2559 
    Google Scholar
  • 5 Felpin F.-X. Miqueu K. Sotiropoulos J.-M. Fouquet E. Ibarguren O. Laudien J. Chem. Eur. J.  2010,  16:  5191 
    Google Scholar
  • 7a Garret CE. Prasad K. Adv. Synth. Catal.  2004,  346:  889 
    Google Scholar
  • 7b Welch CJ. Albaneze-Walker J. Leornard WR. Biba M. DaSilva J. Henderson D. Laing B. Mathre DJ. Spencer S. Bu X. Wang T. Org. Process Res. Dev.  2005,  9:  198 
    Google Scholar
  • 8 Felpin F.-X. Ibarguren O. Nassar-Hardy L. Fouquet E. J. Org. Chem.  2009,  74:  1349 
    Google Scholar
4

Pd(II)/Ceggshell: Palladium nanoparticles distributed close to the surface of the charcoal; BET surface area of approximately 800 m² g-¹; 5 wt% Pd loading on charcoal; 50% water content.

6

The filtered Pd/C catalyst was, however, very active for hydrogenation, hydrogenolysis, and hydrodehalogenation.