Synthesis 2008(6): 995-997  
DOI: 10.1055/s-2007-990934
PSP
© Georg Thieme Verlag Stuttgart · New York

Unsymmetrical Aryl-Aryl Cross-Coupling Leading to 6H-Dibenzopyrans

Elena Mottia, Nicola Della Ca’a, Raffaella Ferracciolib, Marta Catellani*a
a Dipartimento di Chimica Organica e Industriale, Università di Parma, V. le G. P. Usberti 17/A, 43100 Parma, Italy
Fax: +39(0521)905472; e-Mail: marta.catellani@unipr.it;
b CNR-Istituto di Scienze e Tecnologie Molecolari (ISTM), Via C. Golgi 19, 20133 Milano, Italy
Further Information

Publication History

Received 14 August 2007
Publication Date:
28 November 2007 (online)

Abstract

6H-Dibenzopyrans are prepared starting from ortho-substituted aryl iodides, o-bromophenols and activated olefins, in the presence of a catalytic system based on palladium acetate and norbornene by means of a simple and efficient, one-pot, three-component procedure under mild conditions.

    References

  • 1a Qi L. Yamamoto N. Meijler MM. Altobell LJ. Koob GF. Wirsching P. Janda KD. J. Med. Chem.  2005,  48:  7389 
  • 1b Travis CR. inventors; PCT Int. Appl. WO  2004016254.  ; Chem. Abstr. 2004, 140, 193851
  • 1c Melloni P, Salvatori P, and Lovisolo PP. inventors; US Patent  4463001.  ; Chem. Abstr. 1982, 97, 162823
  • 2a Devlin JP. Can. J. Chem.  1975,  53:  343 
  • 2b For a recent three-step procedure, see: Barluenga J. Fananas FJ. Sanz R. Fernandez Y. Chem. Eur. J.  2002,  8:  2034 
  • 3a For the aryl coupling between two equal moieties (symmetrical coupling), see: Motti E. Ippomei GP. Deledda S. Catellani M. Synthesis  2003,  2671 
  • 3b For the aryl coupling between two different moieties (unsymmetrical coupling), see: Faccini F. Motti E. Catellani M. J. Am. Chem. Soc.  2004,  126:  78 
  • 4 Motti E. Faccini F. Ferrari I. Catellani M. Ferraccioli R. Org. Lett.  2006,  8:  3967 
  • 5 Miura M. Tsuda T. Satoh T. Nomura M. Chem. Lett.  1997,  1103