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Synthesis 2008(19): 3099-3107  
DOI: 10.1055/s-2008-1067263
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

A Comparative Study on Stille Cross-Coupling Reactions of 2-Phenylthiazoles and 2-Phenyloxazoles

Johanna Hämmerle, Markus Spina, Michael Schnürch, Marko D. Mihovilovic, Peter Stanetty*
Institute of Applied Synthetic Chemistry, Vienna University of Technology, Getreidemarkt 9/163-OC, 1060 Vienna, Austria
Fax: +43(1)5880115499; e-Mail: peter.stanetty@tuwien.ac.at;
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Publication History

Received 15 April 2008
Publication Date:
05 September 2008 (online)

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Abstract

A systematic study of the cross-coupling capability of the 4- and 5-positions of 2-phenylthiazoles and -oxazoles under Stille conditions is presented. The azoles were both applied as stannanes and as the halide component. The obtained results were compared regarding the position of the halide and Bu3Sn group. In order to establish a general reactivity platform for those heterocyclic systems, a broad variety of aromatic and heteroaromatic halides were coupled and some significant differences concerning the coupling properties of the investigated systems were observed.

Key words

cross-coupling - heterocycles - Stille reaction - oxazole - thiazole

    References

  • Thiazoles:
  • 1a Rivkin A. Cho YS. Gabarda AE. Yoshimura F. Danishefsky SJ. J. Nat. Prod.  2004,  67:  139 
    Google Scholar
  • 1b Bach T. Heuser S. Angew. Chem. Int. Ed.  2001,  40:  3184 
    Google Scholar
  • 1c Plazzi PV. Bordi F. Silva C. Morini G. Caretta A. Barocelli E. Vitali T. Eur. J. Med. Chem.  1995,  30:  881 
    Google Scholar
  • 1d Ganesh T. Schilling JK. Palakodety RK. Ravindra R. Shanker N. Bane S. Kingston DGI. Tetrahedron  2003,  59:  9979 
    Google Scholar
  • 1e Shao J. Panek JS. Org. Lett.  2004,  6:  3083 
    Google Scholar
  • Thiazoles and oxazoles:
  • 1f Nicolaou KC. Roschangar F. Vourloumis D. Angew. Chem. Int. Ed.  1998,  37:  2014 
    Google Scholar
  • 1g Zhong J. Zaiguo L. Runqiu H. Nat. Prod. Rep.  2002,  19:  454 
    Google Scholar
  • 1h Lucke AJ. Tyndall JDA. Singh Y. Fairlie DP. J. Mol. Graphics Modell.  2003,  21:  341 
    Google Scholar
  • Oxazoles:
  • 1i Yeh VSC. Tetrahedron  2004,  60:  11995 
    Google Scholar
  • 2a Hantzsch A. Ber. Dtsch. Chem. Ges.  1888,  21:  942 
    Google Scholar
  • 2b Science of Synthesis   Vol. 11:  Schaumann E. Georg Thieme Verlag; Stuttgart: 2002.  p.627 
    Google Scholar
  • 2c Ghosh AK. Bilcer G. Schiltz G. Synthesis  2001,  2203 
    Google Scholar
  • 2d List B. Castello C. Synlett  2001,  1687 
    Google Scholar
  • 3a The Chemistry of Heterocyclic Compounds   Vol. 60:  Palmer DC. Wiley; New York: 2004. 
    Google Scholar
  • 3b Hassner A. Fischer B. Heterocycles  1993,  35:  1441 
    Google Scholar
  • 3c Turchi IJ. Ind. Eng. Chem. Prod. Res. Dev.  1981,  20:  32 
    Google Scholar
  • 4a Handbook of Organopalladium Chemistry for Organic Synthesis   Vol. 1:  Negishi E. de Meijere A. Wiley; Hoboken N.J.: 2002. 
    Google Scholar
  • 4b Handbook of Organopalladium Chemistry for Organic Synthesis   Vol. 2:  Negishi E. de Meijere A. Wiley; Hoboken N.J.: 2002. 
    Google Scholar
  • 4c Metal-Catalyzed Cross-Coupling Reactions   2nd ed., Vol. 1:  de Meijere A. Diederich F. Wiley-VCH; Weinheim: 2004. 
    Google Scholar
  • 4d Metal-Catalyzed Cross-Coupling Reactions   2nd ed., Vol. 2:  de Meijere A. Diederich F. Wiley-VCH; Weinheim: 2004. 
    Google Scholar
  • 4e Schnürch M. Flasik R. Khan A. Spina M. Mihovilovic MD. Stanetty P. Eur. J. Org. Chem.  2006,  3283 
    Google Scholar
  • 4f Schröter S. Stock C. Bach T. Tetrahedron  2005,  61:  2245 
    Google Scholar
  • Thiazoles:
  • 5a Bach T. Heuser S. Tetrahedron Lett.  2000,  41:  1707 
    Google Scholar
  • 5b Hodgetts KJ. Kershaw MT. Org. Lett.  2002,  4:  1363 
    Google Scholar
  • Oxazoles:
  • 5c Young GL. Smith SA. Taylor RJK. Tetrahedron Lett.  2004,  45:  3797 
    Google Scholar
  • 6a Stille JK. Angew. Chem., Int. Ed. Engl.  1986,  25:  508 
    Google Scholar
  • 6b Nicolaou KC. He F. Roschangar F. King NP. Vourloumis D. Li T. Angew. Chem. Int. Ed.  1998,  37:  84 
    Google Scholar
  • 6c Espinet P. Echavarren AM. Angew. Chem. Int. Ed.  2004,  43:  4704 
    Google Scholar
  • 7 Stanetty P. Schnürch M. Mihovilovic MD. J. Org. Chem.  2006,  71:  3754 
    CrossrefPubMedGoogle Scholar
  • 8 Erlenmeyer H. Becker C. Sorkin E. Bloch H. Suter E. Helv. Chim. Acta  1947,  30:  2058 
    CrossrefPubMedGoogle Scholar
  • 9 Begtrup M. Hansen LBL. Acta Chem. Scand.  1992,  46:  372 
    CrossrefGoogle Scholar
  • For reviews of halogen dance reactions, see:
  • 10a Schnürch M. Spina M. Khan AF. Mihovilovic MD. Stanetty P. Chem. Soc. Rev.  2007,  36:  1046 
    Google Scholar
  • 10b Nora de Souza MV. Curr. Org. Chem.  2007,  11:  637 
    Google Scholar
  • 10c Duan X.-F. Zhang Z.-B. Heterocycles  2005,  65:  2005 
    Google Scholar
  • 10d Fröhlich J. Prog. Heterocycl. Chem.  1994,  6:  1 
    Google Scholar
  • 10e Bunnett JF. Acc. Chem. Res.  1972,  5:  139 
    Google Scholar
  • For halogen dance reactions on thiazole, see:
  • 10f Stanetty P. Schnürch M. Mereiter K. Mihovilovic MD. J. Org. Chem.  2005,  70:  567 
    Google Scholar
  • 10g Stangeland EL. Sammakia T. J. Org. Chem.  2004,  69:  2381 
    Google Scholar
  • 10h Holzweber M. Schnürch M. Stanetty P. Synlett  2007,  3016 
    Google Scholar
  • For halogen dance reactions on oxazole, see:
  • 10i Stanetty P. Spina M. Mihovilovic MD. Synlett  2005,  1433 
    Google Scholar
  • 11 Kashima C. Arao H. Synthesis  1989,  873 
    Article in Thieme ConnectGoogle Scholar
  • 12 Crawforth CM. Fairlamb IJS. Kapdi AR. Serrano JL. Taylor RJK. Sanchez G. Adv. Synth. Catal.  2006,  348:  405 
    CrossrefGoogle Scholar
  • 13 Littke AF. Fu GC. Angew. Chem. Int. Ed.  1999,  38:  2411 
    CrossrefPubMedGoogle Scholar
  • 14a Goodson FE. Wallow TI. Novak BM. J. Am. Chem. Soc.  1997,  119:  12441 
    Google Scholar
  • 14b Grushin VV. Organometallics  2000,  19:  1888 
    Google Scholar
  • 15a Shao J. Panek JS. Org. Lett.  2004,  6:  3083 
    Google Scholar
  • 15b Delgado O. Müller HM. Bach T. Chem. Eur. J.  2008,  14:  2322 
    Google Scholar
  • 16 Littke AF. Fu GC. Angew. Chem. Int. Ed.  2002,  41:  4176 
    Google Scholar
  • 17 Hämmerle J. Schnürch M. Stanetty P. Synlett  2007,  2975 
    Article in Thieme ConnectGoogle Scholar
  • 18 Bach T. Heuser S. J. Org. Chem.  2002,  67:  5789 
    CrossrefPubMedGoogle Scholar
  • 19 Vernin G. Aune JP. Dou HJM. Metzger J. Bull. Soc. Chim. Fr.  1967,  4523 
    Google Scholar
  • 20 Hodgetts KJ. Kershaw MT. Org. Lett.  2002,  4:  1363 
    CrossrefPubMedGoogle Scholar
  • 21 Maeda M. Kojima M. J. Chem. Soc., Perkin Trans. 1  1978,  685 
    CrossrefGoogle Scholar
  • 22 Turner GL. Morris JA. Greaney MF. Angew. Chem. Int. Ed.  2007,  46:  7996 
    CrossrefPubMedGoogle Scholar
  • 23 Kulkarni BS. Fernandez BS. Patel MR. Bellare RA. Deliwala CV. J. Pharm. Sci.  1969,  58:  852 
    CrossrefPubMedGoogle Scholar
  • 24 Singh SP. Sehgal S. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem.  1988,  27:  941 
    Google Scholar
  • 25 Mahjoub AR. Morsali A. Z. Kristallogr. - New Cryst. Struct.  2003,  218:  121 
    Google Scholar
  • 26 Fischer E. Chem. Ber.  1896,  29:  207 
    Google Scholar
  • 27 Keni M. Tepe JJ. J. Org. Chem.  2005,  70:  4211 
    CrossrefPubMedGoogle Scholar
  • 28 Kataoka T. Watanabe S.-I. Yamamoto K. Yoshimatsu M. Tanabe G. Muraoka O. J. Org. Chem.  1998,  63:  6382 
    CrossrefPubMedGoogle Scholar