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

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.

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 

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 

4

Pd(II)/C_eggshell: Palladium nanoparticles distributed close to the surface of the charcoal; BET surface area of approximately 800 m^² g^-¹; 5 wt% Pd loading on charcoal; 50% water content.

5 Felpin F.-X. Miqueu K. Sotiropoulos J.-M. Fouquet E. Ibarguren O. Laudien J. Chem. Eur. J.  2010,  16:  5191 

6

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

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