Download PDF
Synthesis 2010(15): 2553-2566  
DOI: 10.1055/s-0029-1218814
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Palladium-Catalysed Direct Heteroarylation of Bromobenzylacetamide Derivatives: A Simple Access to Heteroarylated Benzylamine Derivatives

Nouria Laidaouia,b, Abdellah Miloudib, Douniazad El Abed*b, Henri Doucet*a
a Institut Sciences Chimiques de Rennes, UMR 6226 CNRS-Université de Rennes ‘Catalyse et Organometalliques’, Campus de Beaulieu, 35042 Rennes, France
Fax: +33(2)23236939; e-Mail: henri.doucet@univ-rennes1.fr;
b Laboratoire de Réactivité et Chimie Fine, Département de Chimie, Faculté des Sciences, Université d’Oran Es-Sénia, BP. 1524, EL M’naouer Oran 31100, Algeria
Further Information

Publication History

Received 23 March 2010
Publication Date:
15 June 2010 (online)

   Permissions and Reprints All articles of this category
Preview

Abstract

The palladium-catalysed direct arylation of bromobenzylacetamide derivatives using a wide variety of heteroaromatics gives a very simple access to heteroarylated benzylacetamides. 2-, 3- and 4-Bromobenzylacetamides present a very similar reactivity. In the presence of 2-subtituted furans, thiophenes, pyrroles, thia­zoles, or imidazoles a regioselective 5-arylation was observed. The reaction of benzoxazole gave the 2-arylated compounds; whereas 3,5-dimethylisoxazole gave the 4-arylated products. In most cases, the system using PdCl(C3H5)(dppb) as the catalyst, KOAc as the base, and DMAC as the solvent gave high yields of coupling products.

Key words

palladium - cross-coupling reaction - arylation - furans - thiophenes - pyrroles - thiazoles - imidazoles - benzoxazoles

    References

  • 1a For examples of palladium cross-coupling with heteroaromatic compounds, see: Li JJ. Gribble GW. Palladium in Heterocyclic Chemistry   Pergamon; Amsterdam: 2000. 
  • 1b Kondolff I. Doucet H. Santelli M. Synlett  2005,  2057 
  • 1c Ackermann L. Modern Arylation Methods   Wiley-VCH; Weinheim: 2009. 
  • 2 Ohta A. Akita Y. Ohkuwa T. Chiba M. Fukunaga R. Miyafuji A. Nakata T. Tani N. Aoyagi Y. Heterocycles  1990,  31:  1951 
    CrossrefSearch in Google Scholar
  • 3a Alberico D. Scott ME. Lautens M. Chem. Rev.  2007,  107:  174 
    Search in Google Scholar
  • 3b Satoh T. Miura M. Chem. Lett.  2007,  36:  200 
    Search in Google Scholar
  • 3c Doucet H. Hierso JC. Curr. Opin. Drug Discovery Dev.  2007,  10:  672 
    Search in Google Scholar
  • 3d Campeau L.-C. Stuart DR. Fagnou K. Aldrichimica Acta  2007,  40:  35 
    Search in Google Scholar
  • 3e Seregin IV. Gevorgyan V. Chem. Soc. Rev.  2007,  36:  1173 
    Search in Google Scholar
  • 3f Li B.-J. Yang S.-D. Shi Z.-J. Synlett  2008,  949 
  • 3g Bellina F. Rossi R. Tetrahedron  2009,  65:  10269 
    Search in Google Scholar
  • 3h Ackermann L. Vincente R. Kapdi AR. Angew. Chem. Int. Ed.  2009,  48:  9792 
    Search in Google Scholar
  • 3i Roger J. Gottumukkala AL. Doucet H. ChemCatChem  2010,  2:  20 
    Search in Google Scholar
  • For recent examples of direct arylations of furans, see:
  • 4a Parisien M. Valette D. Fagnou K. J. Org. Chem.  2005,  70:  7578 
    Search in Google Scholar
  • 4b Lindahl K.-F. Carroll A. Quinn RJ. Ripper JA. Tetrahedron Lett.  2006,  47:  7493 
    Search in Google Scholar
  • 4c Beccalli EM. Broggini G. Martinelli M. Sottocornola S. Synthesis  2008,  136 
  • 4d Gottumukkala AL. Doucet H. Adv. Synth. Catal.  2008,  350:  2183 
    Search in Google Scholar
  • 4e Liégaut B. Lapointe D. Caron L. Vlassova A. Fagnou K. J. Org. Chem.  2009,  74:  1826 
    Search in Google Scholar
  • 4f Dong JJ. Roger J. Pogan F. Doucet H. Green Chem.  2009,  11:  1832 
    Search in Google Scholar
  • 4g Ionita M. Roger J. Doucet H. ChemSusChem  2010,  3:  367 
    Search in Google Scholar
  • For recent examples of direct arylations of thiophenes, see:
  • 5a David E. Pellet-Rostaing S. Lemaire M. Tetrahedron  2007,  63:  8999 
    Search in Google Scholar
  • 5b Chiong HA. Daugulis O. Org. Lett.  2007,  9:  1449 
    Search in Google Scholar
  • 5c Battace A. Lemhadri M. Zair T. Doucet H. Santelli M. Adv. Synth. Catal.  2007,  349:  2507 
    Search in Google Scholar
  • 5d Amaladass P. Clement JA. Mohanakrishnan AK. Tetrahedron  2007,  63:  10363 
    Search in Google Scholar
  • 5e Derridj F. Gottumukkala AL. Djebbar S. Doucet H. Eur. J. Inorg. Chem.  2008,  2550 
  • 5f Nakano M. Tsurugi H. Satoh T. Miura M. Org. Lett.  2008,  10:  1851 
    Search in Google Scholar
  • 5g Roger J. Po˛gan F. Doucet H. Green Chem.  2009,  11:  425 
    Search in Google Scholar
  • 5h Dong JJ. Roger J. Doucet H. Tetrahedron Lett.  2009,  50:  2778 
    Search in Google Scholar
  • For recent examples of direct arylations of pyrroles or indoles, see:
  • 6a Bellina F. Cauteruccio S. Rossi R. Eur. J. Org. Chem.  2006,  1379 
  • 6b Wang X. Gribkov DV. Sames D. J. Org. Chem.  2007,  72:  1476 
    Search in Google Scholar
  • 6c Lebrasseur N. Larrosa I. J. Am. Chem. Soc.  2008,  130:  2926 
    Search in Google Scholar
  • 6d Fall Y. Doucet H. Santelli M. ChemSusChem  2009,  2:  153 
    Search in Google Scholar
  • 6e Roger J. Doucet H. Adv. Synth. Catal.  2009,  351:  1977 
    Search in Google Scholar
  • For recent examples of direct arylations of thiazoles, see:
  • 7a Gottumukkala AL. Doucet H. Eur. J. Inorg. Chem.  2007,  3629 
  • 7b Campeau L.-C. Bertrand-Laperle M. Leclerc J.-P. Villemure E. Gorelsky S. Fagnou K. J. Am. Chem. Soc.  2008,  130:  3276 
    Search in Google Scholar
  • 7c Martin T. Verrier C. Hoarau C. Marsais F. Org. Lett.  2008,  10:  2909 
    Search in Google Scholar
  • 7d Roger J. Po˛gan F. Doucet H. J. Org. Chem.  2009,  74:  1179 
    Search in Google Scholar
  • For recent examples of direct arylations of imidazoles, see:
  • 8a Bellina F. Cauteruccio S. Mannina L. Rossi R. Viel S. Eur. J. Org. Chem.  2006,  693 
  • 8b Cerna I. Pohl R. Klepetarova B. Hocek M. Org. Lett.  2006,  8:  5389 
    Search in Google Scholar
  • 8c Bellina F. Calandri C. Cauteruccio S. Rossi R. Tetrahedron  2007,  63:  1970 
    Search in Google Scholar
  • 8d Bellina F. Cauteruccio S. Di Flore A. Rossi R. Eur. J. Org. Chem.  2008,  5436 
  • 8e Bellina F. Cauteruccio S. Di Flore A. Marchietti C. Rossi R. Tetrahedron  2008,  64:  6060 
    Search in Google Scholar
  • 8f Roger J. Doucet H. Tetrahedron  2009,  65:  9772 
    Search in Google Scholar
  • 9 For recent examples of direct arylations of isoxazoles, see: Fall Y. Reynaud C. Doucet H. Santelli M. Eur. J. Org. Chem.  2009,  4041 
    Crossref
  • For recent examples of direct arylations of oxazoles, see:
  • 10a Hoarau C. Du Fou de Kerdaniel A. Bracq N. Grandclaudon P. Couture A. Marsais F. Tetrahedron Lett.  2005,  46:  8573 
    Search in Google Scholar
  • 10b Turner GL. Morris JA. Greaney MF. Angew. Chem. Int. Ed.  2007,  46:  7996 
    Search in Google Scholar
  • 10c Ohnmacht SA. Mamone P. Culshaw AJ. Greaney MF. Chem. Commun.  2008,  1241 
  • 10d Besselievre F. Mahuteau-Betzer F. Grierson DS. Piguel S. J. Org. Chem.  2008,  73:  3278 
    Search in Google Scholar
  • 10e Verrier C. Hoarau C. Marsais F. Org. Biomol. Chem.  2009,  7:  647 
    Search in Google Scholar
  • 10f Roger J. Verrier C. Le Goff R. Hoarau C. Doucet H. ChemSusChem  2009,  2:  951 
    Search in Google Scholar
  • 10g Besselievre F. Lebrequier S. Mahuteau-Betzer F. Piguel S. Synthesis  2009,  3511 
  • 11a Hennings DD. Iwasa S. Rawal VH. J. Org. Chem.  1997,  62:  2 
    Search in Google Scholar
  • 11b Grigg R. Savic V. Tambyrajah V. Tetrahedron Lett.  2000,  41:  3003 
    Search in Google Scholar
  • 11c Li W.-R. Hsu N.-M. Chou H.-H. Lin ST. Lin Y.-S. Chem. Commun.  2000,  401 
  • 11d Torres JC. Pinto AC. Garden SJ. Tetrahedron  2004,  60:  9889 
    Search in Google Scholar
  • 11e Cuny G. Bois-Choussy M. Zhu J. J. Am. Chem. Soc.  2004,  126:  14475 
    Search in Google Scholar
  • 11f Parisien M. Valette D. Fagnou K. J. Org. Chem.  2005,  70:  7578 
    Search in Google Scholar
  • 11g Campeau L.-C. Parisien M. Jean A. Fagnou K. J. Am. Chem. Soc.  2006,  128:  581 
    Search in Google Scholar
  • 11h Wu J. Nie L. Luo J. Dai W.-M. Synlett  2007,  2728 
  • 12a Shabashov D. Daugulis O. Org. Lett.  2006,  8:  4947 
    Search in Google Scholar
  • 12b Kametani Y. Satoh T. Miura M. Nomura M. Tetrahedron Lett.  2000,  41:  2655 
    Search in Google Scholar
  • 12c Kim J. Jo M. So W. No Z. Tetrahedron Lett.  2009,  50:  1229 
    Search in Google Scholar
  • 13a Murugaiah AMS. Wallinder C. Mahalingam AK. Wu X. Wan Y. Plouffe B. Botros M. Karlen A. Hallberg M. Gallo-Payet N. Alterman M. Bioorg. Med. Chem.  2007,  15:  7166 
    Search in Google Scholar
  • 13b Lee S. Shinji C. Ogura K. Shimizu M. Maeda S. Sato M. Yoshida M. Hashimoto Y. Miyachi H. Bioorg. Med. Chem. Lett.  2007,  17:  4895 
    Search in Google Scholar
  • 13c Hughes TV. Emanuel SL. O’G rady HR. Connolly PJ. Rugg C. Fuentes-Pesquera AR. Karnachi P. Alexander R. Middleton SA. Bioorg. Med. Chem. Lett.  2008,  18:  5130 
    Search in Google Scholar
  • 14 Honda T. Namiki H. Satoh F. Org. Lett.  2001,  3:  631 
    CrossrefSearch in Google Scholar