Download PDF
Synthesis 2011(8): 1249-1254  
DOI: 10.1055/s-0030-1259968
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

A Palladium-Catalyzed Ullmann-Ziegler Cross-Coupling for Sterically Hindered Biaryls

Max P. Nüllen, Richard Göttlich*
Institut für Organische Chemie, Justus Liebig Universität Gießen, Heinrich Buff Ring 58, 35392 Gießen, Germany
Fax: +49(641)9934349; e-Mail: richard.goettlich@org.chemie.uni-giessen.de;
Further Information

Publication History

Received 12 January 2011
Publication Date:
24 March 2011 (online)

    Permissions and Reprints All articles of this category

Abstract

We present a facile and versatile biaryl cross-coupling procedure based on a modified Ullmann coupling that may be applied to a wide range of substrates. This even allows the coupling of sterically hindered substrates under mild reaction conditions.

Key words

biaryls - catalysis - copper - cross-coupling - palladium

    References

  • 1 Huneck S. In Fortschritte der Chemie organischer Naturstoffe /Progress in the Chemistry of Organic Natural Products   Vol. 81:  Herz W. Falk H. Kirby GW. Moore RE. Springer; Wien: 2001. 
    Google Scholar
  • 2a Pu L. Chem. Rev.  1998,  98:  2405 
    Google Scholar
  • 2b Mei X. Wolf C. Chem. Commun.  2004,  2078 
    Google Scholar
  • 2c Mei X. Wolf C. J. Am. Chem. Soc.  2006,  128:  13326 
    Google Scholar
  • 2d Bao X. Snurr RQ. Broadbelt LJ. Langmuir  2009,  25:  10730 
    Google Scholar
  • 3 Horton DA. Bourne GT. Smythe ML. Chem. Rev.  2003,  103:  893 
    CrossrefPubMedGoogle Scholar
  • 4a Waldmann H. He Y.-P. Tan H. Arve L. Arndt H.-D. Chem. Commun.  2008,  5562 
    Google Scholar
  • 4b Zhou J. Bhattacharjee A. Chen S. Chen Y. Duffy E. Farmer J. Goldberg J. Hanselmann R. Ippolito JA. Lou R. Orbin A. Oyelere A. Salvino J. Springer D. Tran J. Wang D. Wu Y. Johnson G. Bioorg. Med. Chem. Lett.  2008,  18:  6179 
    Google Scholar
  • 4c Look GC. Vacin C. Dias TM. Ho S. Tran TH. Lee LL. Wiesner C. Fang F. Marra A. Westmacott D. Hromockyj AE. Murphy MM. Schullek JR. Bioorg. Med. Chem. Lett.  2004,  14:  1423 
    Google Scholar
  • 4d Nicolaou KC. Boddy CNC. Braese S. Winssinger N. Angew. Chem. Int. Ed.  1999,  38:  2096 ; Angew. Chem. 1999, 111, 2230
    Google Scholar
  • 4e Liu G. Fan Y. Carlson JR. Zhao Z.-G. Lam KS. J. Comb. Chem.  2000,  2:  467 
    Google Scholar
  • 5a Croom KF. Keating GM. Am. J. Cardiovasc. Drugs  2004,  4:  395 
    Google Scholar
  • 5b Sharpe M. Jarvis B. Goa KL. Drugs  2001,  61:  1501 
    Google Scholar
  • 6a Hall A. Bit RA. Brown SH. Chaignot HM. Chessell IP. Coleman T. Giblin GMP. Hurst DN. Kilford IR. Lewell XQ. Michel AD. Mohamed S. Naylor A. Novelli R. Skinner L. Spalding DJ. Tang SP. Wilson RJ. Bioorg. Med. Chem. Lett.  2006,  16:  317S 
    Google Scholar
  • 6b Ducharme Y. Blouin M. Carriere M.-C. Chateauneuf A. Cote B. Denis D. Frenette R. Greig G. Kargman S. Lamontagne S. Martins E. Nantel F. O’Neill G. Sawyer N. Metters KM. Friesen RW. Bioorg. Med. Chem. Lett.  2005,  15:  1155 
    Google Scholar
  • 6c dos Santos Filho JM. de Lima JG. Leite LFCC. J. Heterocycl. Chem.  2009,  46:  722 
    Google Scholar
  • 6d Springer DM. Luh BY. Bronson JJ. McElhone KE. Mansuri MM. Gregor KR. Nettleton DO. Stanley PL. Tramposch KM. Bioorg. Med. Chem.  2000,  8:  1087 
    Google Scholar
  • 7a Dagne E. Steglich W. Phytochemistry  1984,  23:  1729 
    Google Scholar
  • 7b Bringmann G. Menche D. Bezabih M. Abegaz BM. Kaminsky R. Planta Med.  1999,  65:  757 
    Google Scholar
  • 8a Trova MP. Barnes KD. Barford C. Benanti T. Bielaska M. Burry L. Lehman JM. Murphy C. O’Grady H. Peace D. Salamone S. Smith J. Snider P. Toporowski J. Tregay S. Wilson A. Wyle M. Zheng X. Friedrich TD. Bioorg. Med. Chem. Lett.  2009,  19:  6608 
    Google Scholar
  • 8b Williams AB. Weiser PT. Hanson RN. Gunther JR. Katzenellenbogen JA. Org. Lett.  2009,  11:  5370 
    Google Scholar
  • 8c Joncour A. Liu J.-M. Decor A. Thoret S. Wdzieczak-Bakala J. Bignon J. Baudoin O. ChemMedChem  2008,  3:  1731 
    Google Scholar
  • 8d Kozikowski AP. Chen Y. Gaysin AM. Savoy DN. Billadeau DD. Kim KH. ChemMedChem  2008,  3:  487 
    Google Scholar
  • 9 Elsenbaumer RL. Shacklette LW. In Handbook of Conducting Polymers   Vol. 1:  Skotheim TA. Elsenbaumer RL. Reynolds JR. Marcel Dekker; New York: 1987.  p.213 
    Google Scholar
  • 10 Su S.-J. Tanaka D. Li Y.-J. Sasabe H. Takeda T. Kido J. Org. Lett.  2008,  10:  941 
    CrossrefPubMedGoogle Scholar
  • 11 Vattem DA. Shetty KJ. Food Biochem.  2005,  29:  234 
    CrossrefGoogle Scholar
  • 12 Sturm N. Hu Y. Zimmermann H. Fritz-Wolf K. Wittlin S. Rahlfs S. Becker K. Antimicrob. Agents Chemother.  2009,  53:  622 
    CrossrefGoogle Scholar
  • 13 Heber D. Cancer Lett.  2008,  269:  262 
    CrossrefGoogle Scholar
  • 14a Iyoda M. Adv. Synth. Catal.  2009,  351:  984 
    Google Scholar
  • 14b Fu GC. Acc. Chem. Res.  2008,  41:  1555 
    Google Scholar
  • 14c Denmark SE. Regens CS. Acc. Chem. Res.  2008,  41:  1486 
    Google Scholar
  • 14d Corbet J.-P. Mignani G. Chem. Rev.  2006,  106:  2651 
    Google Scholar
  • 14e Hassan J. Sévingnon M. Gozzi C. Schulz E. Lemaire M. Chem. Rev.  2002,  102:  1359 
    Google Scholar
  • 14f Bringmann G. Price Mortimer AJ. Keller PA. Gresser MJ. Garner J. Breuning M. Angew. Chem. Int. Ed.  2005,  44:  5384 ; Angew. Chem. 2005, 117, 5518
    Google Scholar
  • 14g Miyaura N. Buchwald SL. Cross-Coupling Reactions. A Practical Guide   Springer; Berlin: 2002. 
    Google Scholar
  • 14h Metal-Catalysed Cross-Coupling Reactions   Diederich F. Stang PJ. Wiley-VCH; Weinheim: 1998. 
    Google Scholar
  • 14i Bringmann G. Walter R. Weirich R. Angew. Chem., Int. Ed. Engl.  1990,  29:  977 ; Angew. Chem. 1990, 102, 1006
    Google Scholar
  • 14j Korn TJ. Knochel P. Angew. Chem. Int. Ed.  2005,  44:  2947 ; Angew. Chem. 2005, 117, 3007
    Google Scholar
  • 15 Ackermann L. Vicente R. Kapdi AR. Angew. Chem. Int. Ed.  2009,  48:  9792 ; Angew. Chem. 2009, 121, 9976
    CrossrefPubMedGoogle Scholar
  • 16 Bringmann G. Gulder T. Gulder TAM. Breuning M. Chem. Rev.  2011,  111:  563 
    CrossrefPubMedGoogle Scholar
  • 17 Ullmann F. Bielecki J. Ber. Dtsch. Chem. Ges.  1901,  34:  2174 
    Google Scholar
  • 18a Ziegler FE. Fowler KW. J. Org. Chem.  1976,  41:  1564 
    Google Scholar
  • 18b Ziegler FE. Fowler KW. Kanfer S. J. Am. Chem. Soc.  1976,  98:  8282 
    Google Scholar
  • 19 Ziegler FE. Fowler KW. Rodgers WB. Wester RT. Org. Synth.  1987,  65:  108 
    Google Scholar
  • 20 Zhang SJ. Zhang DW. Liebeskind LS. J. Org. Chem.  1997,  62:  2312 
    CrossrefPubMedGoogle Scholar