Download PDF
Synthesis 2012(3): 423-430  
DOI: 10.1055/s-0031-1289659
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

One-Pot Ester Synthesis from Allyl and Benzyl Halides and Alcohols by Palladium-Catalyzed Carbonylation

Sara Tommasi, Serena Perrone, Francesca Rosato, Antonio Salomone, Luiginio Troisi*
Dipartimento di Scienze e Tecnologie Biologiche ed Ambientali, University of Salento, via Prov. le Lecce-Monteroni, 73100 Lecce, Italy
Fax: +39(0832)298732; e-Mail: luigino.troisi@unisalento.it;
Further Information

Publication History

Received 13 October 2011
Publication Date:
29 December 2011 (online)

    Permissions and Reprints All articles of this category

Abstract

A mild and efficient one-pot synthesis of esters based on the Pd-catalyzed alkoxy- and aryloxycarbonylation of allylic and benzylic halides is described. The methodology has been applied to primary, secondary, and tertiary alcohols as well as to phenol derivatives. The O-protection of some biologically relevant molecules is also reported.

Key words

alcohols - allyl halides - benzyl halides - esterification - Pd-catalysis

    References

  • 1a Greene TW. Wuts PGM. Protective Groups in Organic Synthesis   Wiley; New York: 1999. 
  • 1b Larock RC. Comprehensive Organic Transformations   VCH; Weinheim: 1989.  p.966 
  • 2a Dhimitruka I. Santalucia J. Org. Lett.  2006,  8:  47 
    Search in Google Scholar
  • 2b Pittelkow M. Kamounah FS. Boas U. Pedersen B. Christensen JB. Synthesis  2004,  2485 
  • 3a Sakakura A. Kawajiri K. Ohkubo T. Kosugi Y. Ishihara K. J. Am. Chem. Soc.  2007,  129:  14775 
    Search in Google Scholar
  • 3b Kadam ST. Kim SS. Synthesis  2008,  267 
  • 3c Chandra KL. Saravan P. Singh RK. Singh VK. Tetrahedron  2002,  58:  1369 
    Search in Google Scholar
  • 3d Chakraborti AK. Gulhane R. . Synthesis  2004,  111 
  • 3e Khan AT. Choudry LH. Ghosh S. Eur. J. Org. Chem.  2005,  2782 
  • 3f Procopio A. Dalpozzo R. De Nino A. Maiuolo L. Nardi M. Romeo G. Org. Biomol. Chem.  2005,  3:  4129 
    Search in Google Scholar
  • 4a Sano T. Synthesis  1999,  1141 
  • 4b Bassetti M. D’Annibale A. Fanfoni A. Minissi F. Org. Lett.  2005,  7:  1805 
    Search in Google Scholar
  • 5a Luo F. Pan C. Qian P. Cheng J. J. Org. Chem.  2010,  75:  5379 
    Search in Google Scholar
  • 5b Kabawata T. Mizugaki T. Ebitani K. Kaneda K. Tetrahedron Lett.  2003,  44:  9205 
    Search in Google Scholar
  • 6a Akgün N. Yaprakçi A. Candemir C. Eur. J. Lipid Sci. Technol.  2010,  112:  593 
    Search in Google Scholar
  • 6b Liu KJ. Huang YR.
    J. Biotechnol.  2010,  146:  215 
    Search in Google Scholar
  • 7 Georgsson J. Hallberg A. Larhed M. J. Comb. Chem.  2003,  5:  350 
    Search in Google Scholar
  • 8 Zim D. de Souza RF. Dupont J. Monteiro AL. Tetrahedron Lett.  1998,  39:  7071 
    Search in Google Scholar
  • 9 Takahashi T. Inoue H. Tomida S. Doi T. Bray AM. Tetrahedron Lett.  1999,  40:  7843 
    Search in Google Scholar
  • 10a Troisi L. De Vitis L. Granito C. Epifani E. Eur. J. Org. Chem.  2004,  1357 
  • 10b Troisi L. Pindinelli E. De Vitis L. Granito C. Ronzini L. Tetrahedron  2006,  62:  1564 
    Search in Google Scholar
  • 10c Troisi L. Granito C. Pindinelli E. Tetrahedron  2008,  64:  11632 
    Search in Google Scholar
  • 11a Troisi L. Granito C. Rosato F. Videtta V. Tetrahedron Lett.  2010,  51:  371 
    Search in Google Scholar
  • 11b Cacchi S. Fabrizi G. Filisti E. Synlett  2009,  1817 
  • 12 Melchiorre M. Torreggiani A. Chatgilialoglu C. Ferreri C. J. Am. Chem. Soc.  2011,  133:  1584 
    Search in Google Scholar
  • 13 Gambacorta A. Tofani D. Migliorini A. Molecules  2007,  12:  1762 
    Search in Google Scholar
  • 14 Campos JL. De Giovani WF. Romero JR. Synthesis  1990,  597 
  • 15 Ryan SJ. Zhang Y. Kennan AJ. Org. Lett.  2005,  7:  4765 
    Search in Google Scholar
  • 16 Munch-Petersen JON. J. Org. Chem.  1957,  22:  170 
    Search in Google Scholar
  • 17 Kindt-Larsen T. Bitsch V. Krogh A. Inger G. Jart A. Munch-Petersen JON. Acta Chem. Scand.  1963,  17:  1426 
    Search in Google Scholar
  • 18 Davies SG. Mulvaney AW. Russell AJ. Smith AD. Tetrahedron: Asymmetry  2007,  18:  1554 
    Search in Google Scholar
  • 19 Orsini F. Pelizzoni F. Ricca G. Synth. Commun.  1982,  12:  1147 
    Search in Google Scholar
  • 20 Tamura R. Shimizu H. Ono N. Azuma N. Suzuki H. Organometallics  1992,  11:  954 
    Search in Google Scholar
  • 21 Russell AE. Fuller NO. Taylor SJ. Aurriset PJ. Morken P. Org. Lett.  2004,  6:  2309 
    Search in Google Scholar
  • 22 Cai M.-Z. Song C.-S. Huang X. J. Chem. Soc., Perkin Trans. 1  1997,  16:  2273 
    Search in Google Scholar
  • 23 Liu C. He C. Shi W. Chen M. Lei A. Org. Lett.  2007,  9:  5601 
    Search in Google Scholar
  • 24 Olah GA. VanVliet DS. Wang Q. Prakash GKS. Synthesis  1995,  159