Download PDF
Synthesis 2010(3): 515-519  
DOI: 10.1055/s-0029-1217129
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

A Convenient Two-Step Synthesis of 2-Arylbenzofurans

Xin-Fang Duan*, Jian-Xia Feng, Zhan-Bin Zhang
Department of Chemistry, Beijing Normal University, Beijing, 100875, P. R. of China
Fax: +86(10)58802075; e-Mail: xinfangduan@vip.163.com;
Further Information

Publication History

Received 15 September 2009
Publication Date:
20 November 2009 (online)

    Permissions and Reprints All articles of this category

Abstract

A novel and convenient two-step synthesis of 2-arylbenzofurans is described which proceeds via a selective cross-pinacol-type coupling between a salicylaldehyde and an aromatic aldehyde, followed by an acid-promoted cyclization. One advantage of this method is that separation of the three possible pinacol products that can form during the cross-coupling is not necessary. This method is also applied to the synthesis of the 2-arylbenzofuran-containing natural product, homoegonol.

Key words

pinacols - pinacol-type coupling - cross-coupling - benzofurans - 2-arylbenzofurans

    References

  • 1a Friedrichsen W. In Comprehensive Heterocyclic Chemistry II   Vol. 2:  Katritzky AR. Rees CW. Scriven EFV. Pergamon Press; Oxford: 1996.  p.259 
    Google Scholar
  • 1b Donnelly DMX. Meegan MJ. In Comprehensive Heterocyclic Chemistry   Vol. 4:  Katritzky AR. Rees CW. Pergamon Press; London: 1984.  p.531 
    Google Scholar
  • 1c Cagniant P. Cagniant D. In Advances in Heterocyclic Chemistry   Vol. 18:  Katritzky AR. Boulton AJ. Academic Press; New York: 1975.  p.337 
    Google Scholar
  • 1d Hou X.-L. Yang Z. Yeung K.-S. Wong HNC. Prog. Heterocycl. Chem.  2005,  17:  142 
    Google Scholar
  • 1e Hou X.-L. Yang Z. Wong HNC. Prog. Heterocycl. Chem.  2003,  15:  167 
    Google Scholar
  • 1f McCallion GD. Curr. Org. Chem.  1999,  3:  67 
    Google Scholar
  • For selected recent references, see:
  • 2a Csekei M. Novak Z. Kotschy A. Tetrahedron  2008,  64:  8992 
    Google Scholar
  • 2b Takashi O. Daisuke N. Rie T. Akimori W. Org. Lett.  2008,  10:  4967 
    Google Scholar
  • 2c Grigg R. Sridharan V. Sykes DA. Tetrahedron  2008,  64:  8952 
    Google Scholar
  • 2d Chen P. Wang J. Liu K. Li C. J. Org. Chem.  2008,  73:  339 
    Google Scholar
  • 2e Roberta B. Sandro C. Ilse DS. Giancarlo F. Synthesis  2007,  873 
    Google Scholar
  • 2f Russo O. Messaoudi S. Hamze A. Olivi N. Peyrat J.-F. Brion J.-D. Sicsic S. Isabelle B.-B. Alami M. Tetrahedron  2007,  63:  10671 
    Google Scholar
  • 2g Li J.-H. Li J.-L. Wang D.-P. Pi S.-F. Xie Y.-X. Zhang M.-B. Hu X.-C. J. Org. Chem.  2007,  72:  2053 
    Google Scholar
  • 3a Ackermann L. Kaspar LT. J. Org. Chem.  2007,  72:  6149 
    Google Scholar
  • 3b Willis MC. Taylor D. Gillmore AT. Tetrahedron  2006,  62:  11513 
    Google Scholar
  • 3c Carril M. SanMartin R. Tellitu I. Dominguez E. Org. Lett.  2006,  8:  1467 
    Google Scholar
  • 3d Fang Y. Li C. J. Org. Chem.  2006,  71:  6427 
    Google Scholar
  • 3e Chen C.-Y. Dormer PG. J. Org. Chem.  2005,  70:  6964 
    Google Scholar
  • 3f Martinez A. Fernandez M. Estevez JC. Estevez RJ. Castedo L. Tetrahedron  2005,  61:  1353 
    Google Scholar
  • 3g Willis MC. Taylor D. Gillmore AT. Org. Lett.  2004,  6:  4755 
    Google Scholar
  • 4a Franck P. Hostyn S. Beata DH. Agnes PB. Monsieurs K. Matyus P. Maes BUW. Tetrahedron  2008,  64:  6030 
    Google Scholar
  • 4b Ebisawa M. Ueno M. Oshima Y. Kondo Y. Tetrahedron Lett.  2007,  48:  8918 
    Google Scholar
  • 4c Prado S. Toum V. Brigitte SJ. Michel S. Koch M. Cole ST. Tillequin F. Janin YL. Synthesis  2007,  1566 
    Google Scholar
  • For I2-mediated cyclizations, see:
  • 5a Pan C.-F. Yu J. Zhou Y.-Q. Wang Z.-Y. Zhou M.-M. Synlett  2006,  1657 
    Google Scholar
  • For the cyclization using DDQ, see:
  • 5b Takeshi K. Koji I. Heterocycles  2005,  65:  1641 
    Google Scholar
  • 5c Fujita M. Qi G.-Z. Verkerk UH. Dzwiniel TL. McDonald R. Stryker JM. Org. Lett.  2004,  6:  2653 
    Google Scholar
  • For other reagents, see:
  • 5d Aslam SN. Stevenson PC. Phythian SJ. Veitch NC. Hall DR. Tetrahedron  2006,  62:  4214 
    Google Scholar
  • 5e Lattanzi A. Senatore A. Massa A. Scettri A. J. Org. Chem.  2003,  68:  3691 
    Google Scholar
  • 6a 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 
    Google Scholar
  • 6b Mashraqui SH. Patil MB. Sangvikar Y. Ashraf M. Mistry HD. Daub ETH. Meetsma A. J. Heterocycl. Chem.  2005,  42:  947 
    Google Scholar
  • 6c Jørgensen M. Krebs FC. Bechgaard K. J. Org. Chem.  2000,  65:  8783 
    Google Scholar
  • 7a Rele S. Talukdar S. Banerji A. Chattopadhyay S. J. Org. Chem.  2001,  66:  2990 
    Google Scholar
  • 7b Furstner A. Hupperts A. J. Am. Chem. Soc.  1995,  117:  4468 
    Google Scholar
  • 7c Furstner A. Hupperts A. Rock A. Janssen E. J. Org. Chem.  1994,  59:  5215 
    Google Scholar
  • 8a Yuan Y. Men H.-B. Lee C. J. Am. Chem. Soc.  2004,  126:  14720 
    Google Scholar
  • 8b Katerina C. Miloslav N. Pavel P. Jiri S. Collect. Czech. Chem. Commun.  2000,  65:  1939 
    Google Scholar
  • 8c Jean G. Nicole B. Pierre D. J. Heterocycl. Chem.  1990,  27:  10 
    Google Scholar
  • 9a Duan XF. Zeng J. Lü JW. Zhang ZB. J. Org. Chem.  2006,  71:  9873 
    Google Scholar
  • 9b Duan XF. Zeng J. Lü JW. Zhang ZB. Synthesis  2007,  713 
    Google Scholar
  • 9c Duan XF. Zeng J. Zhang ZB. Zi GF. J. Org. Chem.  2007,  72:  10283 
    Google Scholar
  • 10 Duan XF. Feng JX. Zi GF. Zhang ZB. Synthesis  2009,  277 
    Article in Thieme ConnectGoogle Scholar
  • 11a Segal R. Ilana MG. Sokoloff S. Zaitschek DV. J. Chem. Soc. C  1967,  2402 
    Google Scholar
  • 11b Schreiber FG. Stevenson R. Chem. Lett.  1975,  1257 
    Google Scholar
  • 11c Schreiber FG. Stevenson R. J. Chem. Soc., Perkin Trans. 1  1976,  1514 
    Google Scholar
  • 11d Teles HL. Hemerly JP. Pauletti PM. Pandolfi JRC. Araujo AR. Valentini SR. Young MCM. Bolzani VS. Silva DHS. Nat. Prod. Res.  2005,  19:  319 
    Google Scholar
  • 13 Fürstner A. Davies PW. J. Am. Chem. Soc.  2005,  127:  15024 
    Google Scholar
  • 14 Date M. Kawanishi K. Hori T. Watanabe M. Furukawa S. Chem. Pharm. Bull.  1989,  37:  2884 
    CrossrefGoogle Scholar
  • 15 Farago J. Kotschy A. Synthesis  2009,  85 
    Article in Thieme ConnectGoogle Scholar
12

In several of the reactions, a small amount of alkenes formed as byproducts during the cross-coupling which hindered the acid-promoted cyclization of the pinacol products. Although it was not necessary to separate the three pinacols, the alkene by-product was removed by chromatography.