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Synthesis 2009(1): 85-90  
DOI: 10.1055/s-0028-1083261
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Benzo[b]furans by Palladium-NHC Catalyzed Ring Closure of o-Bromobenzyl Ketones

János Faragó, András Kotschy*
Institute of Chemistry, Eötvös Loránd University, Pázmány Péter sétány 1/A, 1117 Budapest, Hungary
Fax: +36(1)8812011; e-Mail: andras.kotschy@hu.netgrs.com;
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Publikationsverlauf

Received 20 October 2008
Publikationsdatum:
12. Dezember 2008 (online)

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Abstract

The palladium-catalyzed ring closure of aryl o-bromo­benzyl ketones, easily accessible from aromatic aldehydes and 2-bromobenzyl bromide, provides a straightforward route to 2-arylbenzofurans. A study of the ring closure revealed that a heterocyclic carbene based catalyst provides the best results.

Key words

ring closure - palladium - catalysis - benzofurans

    References

  • 3a Comprehensive Heterocyclic Chemistry II   Vol. 2:  Katritzky AR. Rees CW. Scriven EFV. Pergamon; Oxford: 1996.  p.259 
  • 3b Comprehensive Heterocyclic Chemistry   Vol. 4:  Katritzky AR. Rees CW. Pergamon; London: 1984.  p.531 
  • 3c Cagniant P. Cagniant D. In Advances in Heterocyclic Chemistry   Vol. 18:  Katritzky AR. Boulton AJ. Academic Press; New York: 1975.  p.337 
    Suche in Google Scholar
  • 3d Schneiders GE. Stevenson R. J. Org. Chem.  1979,  44:  4710 
    Suche in Google Scholar
  • 4a Cacchi S. Fabrizi G. Goggiamani A. Curr. Org. Chem.  2006,  10:  1423 
    Suche in Google Scholar
  • 4b Zeni G. Larock RC. Chem. Rev.  2006,  106:  4644 
    Suche in Google Scholar
  • 4c Hou X.-L. Yang Z. Yeung K.-S. Wong HNC. Prog. Heterocycl. Chem.  2005,  17:  142 
    Suche in Google Scholar
  • 4d Hou X.-L. Yang Z. Wong HNC. Prog. Heterocycl. Chem.  2003,  15:  167 
    Suche in Google Scholar
  • 4e Dell CP. In Science of Synthesis   Vol. 10:  Thomas EJ. Thieme; Stuttgart: 2001.  p.11 
    Suche in Google Scholar
  • 5a Aslam SN. Stevenson PC. Phytian SJ. Veitch NC. Hall DR. Tetrahedron  2006,  62:  4214 
    Suche in Google Scholar
  • 5b Novák Z. Timári G. Kotschy A. Tetrahedron  2003,  59:  7509 
    Suche in Google Scholar
  • 5c Yao T.-L. Yue D.-W. Larock RC. J. Org. Chem.  2005,  70:  9985 
    Suche in Google Scholar
  • 5d Csékei M. Novák Z. Timári G. Kotschy A. ARKIVOC  2004,  (vii):  285 
    Suche in Google Scholar
  • 5e Jinno S. Okita T. Inouye K. Bioorg. Med. Chem. Lett.  1999,  9:  1029 
    Suche in Google Scholar
  • 5f Sakai A. Aoyama S. Shioiri T. Tetrahedron Lett.  1999,  40:  4211 
    Suche in Google Scholar
  • 5g Beutler U. Mazacek J. Penn G. Schenkel B. Wasmuth D. Chimia  1996,  50:  154 
    Suche in Google Scholar
  • 6a Nakamura M. Ilies L. Otsubo S. Nakamura E. Org. Lett.  2006,  8:  2803 
    Suche in Google Scholar
  • 6b Belting V. Krause N. Org. Lett.  2006,  8:  4489 
    Suche in Google Scholar
  • 6c Yue D.-W. Yao T.-L. Larock RC. J. Org. Chem.  2005,  70:  10292 
    Suche in Google Scholar
  • 7a Pan C.-F. Yu J. Zhou Y.-Q. Wang Z.-Y. Zhou M.-M. Synlett  2006,  1657 
  • 7b Fujita M. Qi G.-Z. Verkerk UH. Dzwiniel TL. McDonald R. Stryker JM. Org. Lett.  2004,  6:  2653 
    Suche in Google Scholar
  • 7c Merlini L. Cardillo G. Cricchio R. Tetrahedron  1971,  27:  1875 
    Suche in Google Scholar
  • 7d Lattanzi A. Senatore A. Massa A. Scettri A. J. Org. Chem.  2003,  68:  3691 
    Suche in Google Scholar
  • 8a Shen Q. Peng Q. Shao J.-L. Liu X.-L. Huang Z.-H. Pu X.-Z. Ma L. Li Y.-M. Chan ASC. Gu L.-Q. Eur. J. Med. Chem.  2005,  40:  1307 
    Suche in Google Scholar
  • 8b Mashraqui SH. Patil MB. Sangvikar Y. Ashraf M. Mistry HD. Daub ETH. Meetsma A. J. Heterocycl. Chem.  2005,  42:  947 
    Suche in Google Scholar
  • 8c Santini C. Berger GD. Han W. Mosley R. MacNaul K. Berger J. Doebber T. Wu M. Moller DE. Tolman RL. Sahoo SP. Bioorg. Med. Chem. Lett.  2003,  13:  1277 
    Suche in Google Scholar
  • 8d Jorgensen M. Krebs FC. Bechgaard K. J. Org. Chem.  2000,  65:  8783 
    Suche in Google Scholar
  • 9a Duan X.-F. Zeng J. Zhang Z.-B. Zi G.-F. J. Org. Chem.  2007,  72:  10283 
    Suche in Google Scholar
  • 9b Yuan Y. Men H.-B. Lee C. J. Am. Chem. Soc.  2004,  126:  14720 
    Suche in Google Scholar
  • 9c Rele S. Talukdar S. Banerji A. Chattopadhyay S. J. Org. Chem.  2001,  66:  2990 
    Suche in Google Scholar
  • 9d Fürstner A. Hupperts A. J. Am. Chem. Soc.  1995,  117:  4468 
    Suche in Google Scholar
  • 9e Banerji A. Nayak SK. J. Chem. Soc., Chem. Commun.  1990,  150 
  • 9f Jean G. Nicole B. Pierre D. J. Heterocycl. Chem.  1990,  27:  10 
    Suche in Google Scholar
  • 10a Chen C.-y. Dormer PG. J. Org. Chem.  2005,  70:  6964 
    Suche in Google Scholar
  • 10b Carril M. SanMartin R. Tellitu I. Dominguez E. Org. Lett.  2006,  8:  1467 
    Suche in Google Scholar
  • 10c Ackermann L. Kaspar LT. J. Org. Chem.  2007,  72:  6149 
    Suche in Google Scholar
  • 11 Vincze Z. Bíró AB. Csékei M. Timári G. Kotschy A. Synthesis  2006,  1375 
    Thieme Connect
  • 12a Willis MC. Taylor D. Gillmore AT. Org. Lett.  2004,  6:  4755 
    Suche in Google Scholar
  • 12b Willis MC. Taylor D. Gillmore AT. Tetrahedron  2006,  62:  11513 
    Suche in Google Scholar
  • 13 Khan AT. Mondal E. Sahu PR. Islam S. Tetrahedron Lett.  2003,  44:  919 
    CrossrefSuche in Google Scholar
  • 14a de la Fuente MC. Castedo L. Dominguez D. J. Org. Chem.  1996,  61:  5818 
    Suche in Google Scholar
  • 14b Garcia A. Castedo L. Dominguez D. Tetrahedron  1995,  51:  8585 
    Suche in Google Scholar
  • 14c Lamas C. Garcia A. Castedo L. Dominguez D. Tetrahedron Lett.  1989,  30:  6927 
    Suche in Google Scholar
  • 15 Wei W.-G. Yao Z.-J. J. Org. Chem.  2005,  70:  4585 
    CrossrefPubMedSuche in Google Scholar
  • 16 Smith PM. Thomas EJ. J. Chem. Soc., Perkin Trans. 1  1998,  3541 
    Crossref
  • 17 Baumgartner MT. Jimenez LB. Pierini AB. Rossi RA. J. Chem. Soc., Perkin Trans. 2  2002,  1092 
    Crossref
  • 18 Baxendale IR. Griffiths-Jones CM. Ley SV. Tranmer GK. Chem. Eur. J.  2006,  12:  4407 
    CrossrefSuche in Google Scholar
  • 19 Miyata O. Takeda N. Naito T. Org. Lett.  2004,  6:  1761 
    CrossrefPubMedSuche in Google Scholar
  • 20 Arcadi A. Cacchi S. Rosario MD. Fabrizi G. Marinelli F. J. Org. Chem.  1996,  61:  9280 
    Suche in Google Scholar
  • 21 Raspanti G. inventors; US  5362481.  ; Chem. Abstr. 1994, 122, 187375
1

New address: J. Faragó, Gedeon Richter Chemical Works, Gyömröi út 19-21, Budapest, Hungary.

2

New address: A. Kotschy, Servier Research Institute of Medicinal Chemistry, Záhony u. 7, 1031 Budapest, Hungary.