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: [email protected];
Further Information

Publication History

Received 9 September 2011
Publication Date:
03 November 2011 (online)

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.

    References

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

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

6

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