Download PDF
Synthesis 2009(3): 508-510  
DOI: 10.1055/s-0028-1083293
PSP
© Georg Thieme Verlag Stuttgart ˙ New York

Suzuki-Miyaura Cross-Couplings Mediated by trans-PdBr(N-Succ)(PPh3)2: A Convenient Synthetic Method for Diarylmethanes and Aryl(heteroaryl)methanes

Ian J. S. Fairlamb*, Petr Sehnal, Richard J. K. Taylor*
Department of Chemistry, University of York, Heslington, York, YO10 5DD, UK
Fax: +44(1904)432516; e-Mail: ijsf1@york.ac.uk; e-Mail: rjkt1@york.ac.uk;
Further Information

Publication History

Received 4 September 2008
Publication Date:
19 December 2008 (online)

    Permissions and Reprints All articles of this category

Abstract

Diarylmethanes can be accessed efficiently by Suzuki-Miyaura cross-couplings of arylboronic acids with benzyl halides mediated by trans-PdBr(N-Succ)(PPh3)2. The methodology can be applied to the synthesis of aryl(heteroaryl)methanes.

Key words

catalysis - palladium - pseudohalide - phosphine

    References

  • 1 Metal-Catalyzed Cross-Coupling Reactions   2nd ed.:  de Meijere A. Diederich F. Wiley-VCH; New York: 2004. 
    Google Scholar
  • 2 Transition Metals for Organic Synthesis   2nd ed., Vol. 1:  Beller M. Bolm C. Wiley-VCH; Weinheim: 2004. 
    Google Scholar
  • 3 Nguyen H. Huang X. Buchwald SL. J. Am. Chem. Soc.  2003,  125:  11818 ; and references cited therein
    CrossrefGoogle Scholar
  • 4 Zapf A. Beller M. Chem. Commun.  2005,  431 
    CrossrefGoogle Scholar
  • 5 Bedford RB. Chem. Commun.  2003,  1787 
    CrossrefGoogle Scholar
  • 6 O’Brien CJ. Kantchev EAB. Hadei N. Valente C. Chass GA. Nasielski JC. Lough A. Hopkinson AC. Organ MG. Chem. Eur. J.  2006,  12:  4743 ; and references cited therein
    CrossrefGoogle Scholar
  • 7a Fairlamb IJS. Kapdi AR. Lynam JM. Taylor RJK. Whitwood AC. Tetrahedron  2004,  60:  5711 
    Google Scholar
  • 7b Chaignon NM. Fairlamb IJS. Kapdi AR. Taylor RJK. Whitwood AC. J. Mol. Catal. A: Chem.  2004,  219:  191 
    Google Scholar
  • 7c Serrano JL. Fairlamb IJS. Sánchez G. García L. Pérez J. Vives J. López G. Crawforth CM. Taylor RJK. Eur. J. Inorg. Chem.  2004,  2706 
    Google Scholar
  • 7d Crawforth CM. Fairlamb IJS. Kapdi AR. Serrano JL. Taylor RJK. Sanchez G. Adv. Synth. Catal.  2006,  348:  405 
    Google Scholar
  • 7e Young GL. Smith SA. Taylor RJK. Tetrahedron Lett.  2004,  45:  3797 
    Google Scholar
  • 7f Fairlamb IJS. Taylor RJK. Serrano JL. Sanchez G. New J. Chem.  2006,  30:  1685 
    Google Scholar
  • 8a McPhail KL. Rivett DEA. Lack DE. Davies-Coleman MT. Tetrahedron  2000,  56:  9391 
    Google Scholar
  • 8b Long Y.-Q. Jiang X.-H. Dayam R. Sachez T. Shoemaker R. Sei S. Neamati N. J. Med. Chem.  2004,  47:  2561. 
    Google Scholar
  • 9a Botella L. Nájera C. J. Organomet. Chem.  2002,  663:  46 
    Google Scholar
  • 9b Alonso DA. Nájera C. Pacheco MC. J. Org. Chem.  2002,  67:  5588 
    Google Scholar
  • 10 Burns MJ. Fairlamb IJS. Kapdi AR. Sehnal P. Taylor RJK. Org. Lett.  2007,  9:  5397 
    CrossrefGoogle Scholar
  • 11 Henry N. Enguehard-Gueiffier C. Thery I. Gueiffier A. Eur. J. Org. Chem.  2008,  4824 
    CrossrefGoogle Scholar
  • 12 McLaughlin M. Org. Lett.  2005,  7:  4875 
    CrossrefGoogle Scholar
  • 13 Yi W.-B. Cai C. J. Fluorine Chem.  2005,  126:  831 
    CrossrefGoogle Scholar