Download PDF
Synthesis 2011(14): 2208-2214  
DOI: 10.1055/s-0030-1260666
SPECIALTOPIC
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Functionalized Benzofurans by a Double Heck Reaction of 2,3-Dibromofurans and Subsequent 6π-Electrocyclization/Dehydrogenation

Ghazwan Ali Salmana, Asad Alia,b, Munawar Hussaina, Rasheed Ahmad Kheraa,c, Peter Langer*a,d
a Institut für Chemie, Universität Rostock, Albert-Einstein-Str. 3a, 18059 Rostock, Germany
b Department of Chemistry, University of Mardan, Mardan, Pakistan
c Department of Chemistry, University Faisalabad, Government College, Faisalabad, Pakistan
d Leibniz-Institut für Katalyse an der Universität Rostock e.V., Albert-Einstein-Str. 29a, 18059 Rostock, Germany
Fax: +49(381)4986412; e-Mail: peter.langer@uni-rostock.de;
Further Information

Publication History

Received 14 March 2011
Publication Date:
09 June 2011 (online)

    Permissions and Reprints All articles of this category

Abstract

The twofold Heck reaction of 2,3-dibromofurans afforded 2,3-di(alkenyl)furans which were transformed into functionalized benzofurans by a domino 6π-electrocyclization/dehydrogenation reaction.

Key words

catalysis - palladium - Heck reaction - electrocyclization - furans

    References

  • 1a Miyata O. Takeda N. Morikami Y. Naito T. Org. Biomol. Chem.  2003,  1:  254 
    Search in Google Scholar
  • 1b Xie X. Chen B. Lu J. Han J. She X. Pan X. Tetrahedron Lett.  2004,  45:  6235 
    Search in Google Scholar
  • 1c Zhang H. Ferreira EM. Stoltz BM. Angew. Chem. Int. Ed.  2004,  43:  6144 
    Search in Google Scholar
  • 1d Hagiwara H. Sato K. Nishino D. Hoshi T. Suzuki T. Ando M. J. Chem. Soc., Perkin Trans. 1  2001,  2946 
  • For a review, see:
  • 1e Butin AV. Gutnow AV. Abaev VT. Krapivin GD. Molecules  1999,  4:  52 
    Search in Google Scholar
  • 1f Fuerst DE. Stoltz BM. Wood JL. Org. Lett.  2000,  2:  3521 
    Search in Google Scholar
  • 1g Schneider B. Phytochemistry  2003,  64:  459 
    Search in Google Scholar
  • 1h Katritzky AR. Kirichenkok K. Ji Y. Steel PJ. Karelson M. ARKIVOC  2003,  (vi):  49 
    Search in Google Scholar
  • 2a Wendt B. Ha HR. Hesse M. Helv. Chim. Acta  2002,  85:  2990 
    Search in Google Scholar
  • 2b Carlsson B. Singh BN. Temciuc M. Nilsson S. Li YL. Mellin C. Malm J. J. Med. Chem.  2002,  45:  623 ; and references cited therein
    Search in Google Scholar
  • 2c Kwiecien H. Baumann E. J. Heterocycl. Chem.  1997,  34:  1587 
    Search in Google Scholar
  • 2d Larock RC. Harrison LW. J. Am. Chem. Soc.  1984,  106:  4218 
    Search in Google Scholar
  • 2e Mátyus P. Varga I. Rettegi T. Simay A. Kállay N. Károlyházy L. Kocsis A. Varró A. Pénzes I. Papp JG. Curr. Med. Chem.  2004,  11:  61 
    Search in Google Scholar
  • 2f Wong HNC. Yu P. Yick C.-Y. Pure Appl. Chem.  1999,  71:  1041 
    Search in Google Scholar
  • For longicaudatin, see:
  • 3a Joshi AS. Li X.-C. Nimrod AC. ElSohly HN. Walker LA. Clark AM. Planta Med.  2001,  67:  186 
    Search in Google Scholar
  • For related natural products, see:
  • 3b Sigstad E. Catalan CAN. Diaz JG. Herz W. Phytochemistry  1993,  33:  165 
    Search in Google Scholar
  • 3c Drewes SE. Hudson NA. Bates RB. J. Chem. Soc., Perkin Trans. 1  1987,  2809 
  • For sessiliflorol A, see:
  • 4a Chan JA. Shultis EA. Carr SA. DeBrosse CW. Eggleston DS. J. Org. Chem.  1989,  54:  2098 
    Search in Google Scholar
  • For sessiliflorol B, see:
  • 4b Marston A. Zagorski MG. Hostettmann K. Helv. Chim. Acta  1988,  71:  1210 
    Search in Google Scholar
  • 4c Drewes SE. Hudson NA. Bates RB. Linz GS. Tetrahedron Lett.  1984,  25:  105 
    Search in Google Scholar
  • For flemistrictin E, see:
  • 4d Subrahmanyam K. Rao JM. Vemuri VSS. Babu SS. Roy CP. Rao KVJ. Indian J. Chem., Sect. B  1982,  21:  895 
    Search in Google Scholar
  • For tovophenone C, see:
  • 4e Seo E.-K. Wall ME. Wani MC. Navarro H. Mukherjee R. Farnsworth NR. Kinghorn AD. Phytochemistry  1999,  52:  669 
    Search in Google Scholar
  • For vismiaguianone C, see:
  • 4f Seo E.-K. Wani MC. Wall ME. Navarro H. Mukherjee R. Farnsworth NR. Kinghorn AD. Phytochemistry  2000,  55:  35 
    Search in Google Scholar
  • 4g For piperaduncin B, see ref. 3a and: Bohlmann F. Zdero C. Chem. Ber.  1976,  109:  1436 
    Search in Google Scholar
  • For reviews of cross-coupling reactions of polyhalogenated heterocycles, see:
  • 5a Schröter S. Stock C. Bach T. Tetrahedron  2005,  61:  2245 
    Search in Google Scholar
  • 5b Schnürch M. Flasik R. Khan AF. Spina M. Mihovilovic MD. Stanetty P. Eur. J. Org. Chem.  2006,  3283 
  • 6a Dang TT. Ahmad R. Dang TT. Reinke H. Langer P. Tetrahedron Lett.  2008,  49:  1698 
    Search in Google Scholar
  • 6b Dang TT. Villinger A. Langer P. Adv. Synth. Catal.  2008,  350:  2109 
    Search in Google Scholar
  • 6c Dang TT. Dang TT. Rasool N. Villinger A. Langer P. Adv. Synth. Catal.  2009,  351:  1595 
    Search in Google Scholar
  • 7a Bach T. Krüger L. Tetrahedron Lett.  1998,  39:  1729 
    Search in Google Scholar
  • 7b Bach T. Krüger L. Eur. J. Org. Chem.  1999,  2045 
  • 7c Bach T. Krüger L. Synlett  1998,  1185 
  • 8 de Meijere and co-workers reported twofold Heck reactions of 1,2-dibromocycloalk-1-enes and related substrates and subsequent 6π-electrocyclization; see: Voigt K. von Zezschwitz P. Rosauer K. Lansky A. Adams A. Reiser O. de Meijere A. Eur. J. Org. Chem.  1998,  1521 ; and references cited therein
  • 9a Hussain M. Nguyen TH. Langer P. Tetrahedron Lett.  2009,  50:  3929 
    Search in Google Scholar
  • 9b Tengho Toguem S.-M. Hussain M. Malik I. Villinger A. Langer P. Tetrahedron Lett.  2009,  50:  4962 
    Search in Google Scholar
  • 10 Billingsley K. Buchwald SL. J. Am. Chem. Soc.  2007,  129:  3358 ; and references cited therein
    Search in Google Scholar