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Synthesis 2008(18): 2899-2904  
DOI: 10.1055/s-2008-1067221
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Application of 1-(3-Bromo-3,3-difluoroprop-1-ynyl)benzenes in Diels-Alder Reactions: Synthesis of ortho-CF2Br-Substituted Biaryls

Vasiliy M. Muzalevskiya, Valentine G. Nenajdenko*a, Aleksey V. Shastinb, Elizabeth S. Balenkovaa, Günter Haufe*c
a Department of Chemistry, Moscow State University, Leninskie Gory, Moscow 119992, Russian Federation
e-Mail: nen@acylium.chem.msu.ru;
b Institute of Problems of Chemical Physics, Chernogolovka, Moscow Region 142432, Russian Federation
e-Mail: shastin@icp.ac.ru;
c Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster, Correnstr. 40, 48149 Münster, Germany
Fax: +49(251)8339772; e-Mail: haufe@uni-muenster.de;
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Publication History

Received 26 March 2008
Publication Date:
06 August 2008 (online)

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Abstract

1-(3-Bromo-3,3-difluoroprop-1-ynyl)benzenes were found to be good dienophiles in Diels-Alder reactions. Based on this key reaction a new pathway towards biaryls with an ortho-CF2Br group was elaborated.

Key words

alkynes - biaryls - bicyclic compounds - Diels-Alder reaction­ - fluorine

    References

  • 1a Fringuelli F. Tatticchi A. Dienes in the Diels-Alder Reaction   Wiley; New York: 1990. 
  • 1b Carruthers W. Cycloaddition Reactions in Organic Synthesis   Pergamon Press; Oxford: 1990. 
  • 1c Corey EJ. Guzman-Perez A. Angew. Chem. Int. Ed.  1998,  37:  388; Angew. Chem. 1998, 110, 402 
    Search in Google Scholar
  • 1d Corey EJ. Angew. Chem. Int. Ed.  2002,  41:  1650 ; Angew. Chem. 2002, 114, 1724
    Search in Google Scholar
  • 2 Nicolaou KC. Snyder SA. Montagnon T. Vassilikogiannakis G. Angew. Chem. Int. Ed.  2002,  41:  1668 ; Angew. Chem. 2002, 114, 1742
    CrossrefPubMedSearch in Google Scholar
  • 3a Percy JM. Top. Curr. Chem.  1997,  193:  131 
    Search in Google Scholar
  • 3b Rock MH. In Houben-Weyl, Methods of Organic Chemistry   Vol. E 10b/1:  Baasner B. Hagemann H. Tatlow JC. Thieme; Stuttgart: 1999.  p.513-515  
    Search in Google Scholar
  • 3c Haufe G. Vinyl Fluorides in Cycloadditions, In Fluorine-Containing Synthons, ACS Symposium Series 911   Soloshonok VA. American Chemical Society; Washington DC: 2005.  p.155-172  
  • For example:
  • 4a Ghosh S. Schlosser M. J. Fluorine Chem.  1994,  67:  53 
    Search in Google Scholar
  • 4b Bogachev AA. Kobrina LS. Meyer OGJ. Haufe G. J. Fluorine Chem.  1999,  97:  135 
    Search in Google Scholar
  • For example:
  • 5a Ernet T. Haufe G. Tetrahedron Lett.  1996,  37:  7251 
    Search in Google Scholar
  • 5b Cowley PL. Percy JM. Stanisfield K. Tetrahedron Lett.  1996,  37:  8233 
    Search in Google Scholar
  • 5c Cowley PL. Percy JM. Stanisfield K. Tetrahedron Lett.  1996,  37:  8237 
    Search in Google Scholar
  • 5d Ito H. Saito A. Taguchi T. Tetrahedron: Asymmetry  1998,  9:  1979 
    Search in Google Scholar
  • 5e Ernet T. Maulitz AH. Würthwein E.-U. Haufe G. J. Chem. Soc., Perkin Trans. 1  2001,  1929 
  • 5f Essers M. Mück-Lichtenfeld C. Haufe G. J. Org. Chem.  2002,  67:  4715 
    Search in Google Scholar
  • 5g Haiduch J. Paleta O. Kvíčala J. Haufe G. Eur. J. Org. Chem.  2007,  5101 
  • For example:
  • 6a Chanteau F. Essers M. Plantier-Royon R. Haufe G. Portella C. Tetrahedron Lett.  2002,  43:  1677 
    Search in Google Scholar
  • 6b Gerus I. Tolmachova NA. Vdovenko SI. Fröhlich R. Haufe G. Synthesis  2005,  1269 
  • 6c Leuger J. Blond G. Fröhlich R. Billard T. Haufe G. Langlois BR. J. Org. Chem.  2006,  71:  2735 
    Search in Google Scholar
  • 6d Chanteau F. Plantier-Royon R. Haufe G. Portella C. Tetrahedron  2007,  62:  9049 
    Search in Google Scholar
  • 6e Nenajdenko VG. Muzalevskiy VM. Shastin AV. Balenkova ES. Haufe G. J. Fluorine Chem.  2007,  128:  818 
    Search in Google Scholar
  • 7a Hiyama T. Sato K. Synlett  1990,  53 
  • 7b Ohno T. Ozaki M. Inagaki A. Hirashima T. Nishiguchi I. Tetrahedron Lett.  1993,  34:  2629 
    Search in Google Scholar
  • 8 Ullmann F. Bielecki J. Ber. Dtsch. Chem. Ges.  1901,  34:  2174 
    CrossrefSearch in Google Scholar
  • 9a Suzuki A. Pure Appl. Chem.  1994,  66:  213 
    Search in Google Scholar
  • 9b Miyaura N. Suzuki A. Chem. Rev.  1995,  95:  2457 
    Search in Google Scholar
  • 9c Suzuki A. In Modern Arene Chemistry   Astruc D. Wiley; New York: 2002.  p.53-106  
  • 10 Stille JK. Angew. Chem., Int. Ed. Engl.  1986,  25:  508 ; Angew. Chem. 1986, 98: 504
    Search in Google Scholar
  • 11 Bernis GW. Murcko MA. J. Med. Chem.  1996,  39:  2887 
    CrossrefPubMedSearch in Google Scholar
  • 12a Jacoby E. Bioorg. Med. Chem. Lett.  2002,  12:  891 
    Search in Google Scholar
  • 12b Kutzki O. Park HS. Ernst JT. Omer BP. Yin H. Hamilton AD. J. Am. Chem. Soc.  2002,  124:  11838 
    Search in Google Scholar
  • 12c Ernst JT. Kutzki O. Debnath AK. Jiang S. Lu H. Hamilton AD. Angew. Chem. Int. Ed.  2002,  41:  278 ; Angew. Chem. 2002, 114, 288
    Search in Google Scholar
  • 13a Organofluorine Chemistry. Principles and Commercial Applications   Banks RE. Smart BE. Tatlow JC. Plenum Press; New York: 1994. 
  • 13b Kirsch P. Modern Fluoroorganic Chemistry: Synthesis, Reactivity, Applications   Wiley-VCH; Weinheim: 2004. 
  • 13c Uneyama K. Organofluorine Chemistry   Blackwell; Oxford: 2006. 
  • 13d Current Fluoroorganic Chemistry. New Synthetic Directions, Technologies, Materials, and Biological Applications, ACS Symposium Series 949   Soloshonok VA. Mikami K. Yamazaki T. Welch JT. Honek JF. American Chemical Society; Washington DC: 2006. 
  • 14a Welch JT. Eswarakrishnan S. Fluorine in Bioorganic Chemistry   Wiley; Chichester: 1991. 
  • 14b Organofluorine Compounds in Medicinal Chemistry and Biomedical Applications   Filler R. Kobayashi Y. Yagupolskii LM. Elsevier; Amsterdam: 1993. 
  • 14c Biomedical Frontiers of Fluorine Chemistry, ACS Symposium Series 639   Ojima I. McCarthy JR. Welch JT. American Chemical Society; Washington DC: 1996. 
  • 14d

    Fluorine in the Life Sciences, Multiauthor Special Issue, ChemBioChem 2004, 5, 559-722.

  • 14e

    Fluorine in the Life Science Industry, Multiauthor Special Issue, Chimia 2004, 58, 92-162.

  • 14f Theodoridis G. Fluorine-Containing Agrochemicals: An Overview of Recent Developments, In Advances in Fluorine Science   Vol. 2:  Tressaud A. Elsevier; Amsterdam: 2006.  p.121-175  
    Search in Google Scholar
  • 14g Fluorine and Health. Molecular Imaging, Biomedical Materials and Pharmaceuticals   Tressaud A. Haufe G. Elsevier; Amsterdam: 2008.  p.553-778  
  • 15 Shastin AV. Korotchenko VN. Nenajdenko VG. Balenkova ES. Tetrahedron  2000,  56:  6557 
    CrossrefSearch in Google Scholar
  • 16a Nenajdenko VG. Shastin AV. Korotchenko VN. Varseev GN. Balenkova ES. Eur. J. Org. Chem.  2003,  302 
  • 16b Korotchenko VN. Shastin AV. Nenajdenko VG. Balenkova ES. Tetrahedron  2001,  57:  7519 
    Search in Google Scholar
  • 16c Nenajdenko VG. Varseev GN. Korotchenko VN. Shastin AV. Balenkova ES. J. Fluorine Chem.  2003,  124:  115 
    Search in Google Scholar
  • 16d Nenajdenko VG. Varseev GN. Korotchenko VN. Shastin AV. Balenkova ES. J. Fluorine Chem.  2004,  124:  1339 
    Search in Google Scholar
  • 16e Nenajdenko VG. Varseev GN. Shastin AV. Balenkova ES. J. Fluorine Chem.  2005,  126:  907 
    Search in Google Scholar
  • 16f Shastin AV. Muzalevsky VM. Balenkova ES. Nenajdenko VG. Mendeleev Commun.  2006,  16:  179 
    Search in Google Scholar
  • 17 McCullough JJ. Acc. Chem. Res.  1980,  13:  270 
    CrossrefSearch in Google Scholar
  • 18 Kobayashi Y. Yamashita T. Takahashi K. Kuroda H. Kumadaki I. Tetrahedron Lett.  1982,  23:  343 
    CrossrefSearch in Google Scholar
  • 19 Afarinkia K. Vinader V. Nelson TD. Posner GH. Tetrahedron  1992,  48:  9111 
    CrossrefSearch in Google Scholar
  • 20 Patchett AA. Nargund RP. Ann. Rep. Med. Chem.  2000,  35:  289 
    Search in Google Scholar
  • 21 Bringmann G. Breuning M. Tasler S. Synthesis  1999,  525 ; and references cited therein
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