PDF herunterladen
Synlett 2009(7): 1081-1086  
DOI: 10.1055/s-0028-1088110
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Monoarylation of Dibromoarenes by Simple Palladium Catalyst Systems: Efficient Synthesis of Bromobiaryls from Dibromoarenes and Arylboronic Acids

Cheng-Guo Dong, Tao-Ping Liu, Qiao-Sheng Hu*
Department of Chemistry, College of Staten Island and the Graduate Center, City University of New York, Staten Island, NY 10314, USA
Fax: +1(781)9823910; e-Mail: qiaohu@mail.csi.cuny.edu;
Weitere Informationen

Publikationsverlauf

Received 16 January 2009
Publikationsdatum:
26. März 2009 (online)

   Lizenzen und Reprints Alle Artikel dieser Rubrik

Abstract

The Pd/C/Ph3P- and Pd(PPh3)4/Ph3P-catalyzed cross-couplings of dibromoarenes with arylboronic acids to form bromobiaryls in good to excellent yields are described. Our study showed that readily available Pd/C/Ph3P and Pd(PPh3)4/Ph3P were practically useful catalysts for the synthesis of bromobiaryls from dibromo­arenes.

Key words

palladium - cross-coupling - dibromoarenes - mono­arylation - arylboronic acids

    References and Notes

  • For recent examples, see:
  • 1a Lafrance M. Shore D. Fagnou K. Org. Lett.  2006,  8:  5097 
    Suche in Google Scholar
  • 1b Roberti M. Pizzirani D. Recanatini M. Simoni D. Grimaudo S. Di Cristina A. Abbadessa V. Gebbia N. Tolomeo M. J. Med. Chem.  2006,  49:  3012 
    Suche in Google Scholar
  • 1c Simoni D. Giannini G. Roberti M. Rondanin R. Baruchello R. Rossi M. Grisolia G. Invidiata FP. Aiello S. Marino S. Cavallini S. Siniscalchi A. Gebbia N. Crosta L. Grimaudo S. Abbadessa V. Di Cristina A. Tolomeo M. J. Med. Chem.  2005,  48:  4293 
    Suche in Google Scholar
  • 1d Simoni D. Grisolia G. Giannini G. Roberti M. Rondanin R. Piccagli L. Baruchello R. Rossi M. Romagnoli R. Invidiata FP. Grimaudo S. Jung MK. Hamel E. Gebbia N. Crosta OL. Abbadessa OV. Di Cristina A. Dusonchet L. Meli M. Tolomeo M. J. Med. Chem.  2005,  48:  723 
    Suche in Google Scholar
  • 1e Ju J. Nam H. Jung HM. Lee S. Tetrahedron Lett.  2006,  47:  8673 
    Suche in Google Scholar
  • Selected recent examples, see:
  • 2a Barder TE. Walker SD. Martinelli JR. Buchwald SL. J. Am. Chem. Soc.  2005,  127:  4685 
    Suche in Google Scholar
  • 2b Milne JE. Buchwald SL. J. Am. Chem. Soc.  2004,  126:  13028 
    Suche in Google Scholar
  • 2c Huang X. Anderson KW. Zim D. Jiang L. Klapars A. Buchwald SL. J. Am. Chem. Soc.  2003,  125:  6653 
    Suche in Google Scholar
  • 2d Zim D. Buchwald SL. Org. Lett.  2003,  5:  2413 
    Suche in Google Scholar
  • 2e Parrish CA. Buchwald SL. J. Org. Chem.  2001,  66:  3820 
    Suche in Google Scholar
  • 2f Tomori H. Fox JM. Buchwald SL. J. Org. Chem.  2000,  65:  5334 
    Suche in Google Scholar
  • For recent examples, see:
  • 3a Ashburn BO. Carter RG. Angew. Chem. Int. Ed.  2006,  45:  6737 
    Suche in Google Scholar
  • 3b Feng X. Wu J. Enkelmann V. Muellen K. Org. Lett.  2006,  8:  1145 
    Suche in Google Scholar
  • 3c Dong C.-G. Hu Q.-S. Angew. Chem. Int. Ed.  2006,  45:  2289 
    Suche in Google Scholar
  • 3d Palmer BD. Thompson AM. Booth RJ. Dobrusin EM. Kraker AJ. Lee HH. Lunney EA. Mitchell LH. Ortwine DF. Smaill JB. Swan LM. Denny WA. J. Med. Chem.  2006,  49:  4896 
    Suche in Google Scholar
  • 3e Iwasawa T. Komano T. Tajima A. Tokunaga M. Obora Y. Fujihara T. Tsuji Y. Organometallics  2006,  25:  4665 
    Suche in Google Scholar
  • 3f Yoshikawa S. Odaira J.-i. Kitamura Y. Bedekar AV. Furuta T. Tanaka K. Tetrahedron  2004,  60:  2225 
    Suche in Google Scholar
  • 3g Simoni D. Giannini G. Baraldi PG. Romagnoli R. Roberti M. Rondanin R. Baruchello R. Grisolia G. Rossi M. Mirizzi D. Invidiata FP. Grimaudo S. Tolomeo M. Tetrahedron Lett.  2003,  44:  3005 
    Suche in Google Scholar
  • 4a Transition-Metal-Catalyzed Cross-Coupling Reactions   Diederich F. Stang PJ. Wiley-VCH; New York: 1998. 
  • 4b Beller M. Bolm C. Transition Metals for Organic Synthesis   Wiley-VCH; Weinheim: 1998. 
  • 4c Collman JP. Hegedus LS. Norton JR. Finke RG. Principles and Applications of Organotransition Metal Chemistry   University Science Books; Mill Valley CA: 1987. 
  • 5a Nicolaou KC. Bulger PG. Sarlah D. Angew. Chem. Int. Ed.  2005,  44:  4442 
    Suche in Google Scholar
  • 5b Hu Q.-S. In Synthetic Methods for Step-Growth Polymers   Rogers M. Long T. Wiley; New York: 2003.  p.467-526  
  • For recent examples, see:
  • 6a Blaszczyk A. Fischer M. von Haenisch C. Mayor M. Eur. J. Org. Chem.  2007,  2630 
  • 6b Fürstner A. Kennedy JWJ. Chem. Eur. J.  2006,  12:  7398 
    Suche in Google Scholar
  • 6c Glegola K. Framery E. Pietrusiewicz KM. Sinou D. Adv. Synth. Catal.  2006,  348:  1728 
    Suche in Google Scholar
  • 6d Hilt G. Hess W. Schmidt F. Eur. J. Org. Chem.  2005,  2526 
  • 6e Lee SH. Jang B.-B. Kafafi ZH. J. Am. Chem. Soc.  2005,  127:  9071 
    Suche in Google Scholar
  • 6f Wu J. Baumgarten M. Debije MG. Warman JW. Müllen K. Angew. Chem. Int. Ed.  2004,  43:  5331 
    Suche in Google Scholar
  • 6g Aranyos A. Old DW. Kiyomori A. Wolfe JP. Sadighi JP. Buchwald SL. J. Am. Chem. Soc.  1999,  121:  4369 
    Suche in Google Scholar
  • 7 For an example of using organometallic reagents to control the selectivity between Br group and OTf group for the formation of 2-bromobiaryls, see: Espino G. Kurbangalieva A. Brown JM. Chem. Commun.  2007,  1742 
    Crossref
  • 8a Cheng X. Zhu S.-F. Qiao X.-C. Yan P.-C. Zhou Q.-L. Tetrahedron  2006,  62:  8077 
    Suche in Google Scholar
  • 8b Chiang C.-L. Shu C.-F. Chen C.-T. Org. Lett.  2005,  7:  3717 
    Suche in Google Scholar
  • 8c Chouteau F. Ramanitrahasimbola D. Rasoanaivo P. Chibale K. Bioorg. Med. Chem. Lett.  2005,  15:  3024 
    Suche in Google Scholar
  • 8d Motomura T. Nakamura H. Suginome M. Murakami M. Ito Y. Bull. Chem. Soc. Jpn.  2005,  78:  142 
    Suche in Google Scholar
  • 8e Cheng X. Hou G.-H. Xie J.-H. Zhou Q.-L. Org. Lett.  2004,  6:  2381 
    Suche in Google Scholar
  • 8f Berthiol F. Kondolff I. Doucet H. Santelli M. J. Organomet. Chem.  2004,  689:  2786 
    Suche in Google Scholar
  • 8g Nishimura M. Ueda M. Miyaura N. Tetrahedron  2002,  58:  5779 
    Suche in Google Scholar
  • Polymer-supported substrates or ligands/catalysts:
  • 9a Rasmussen LK. Begtrup M. Ruhland T. J. Org. Chem.  2006,  71:  1230 
    Suche in Google Scholar
  • 9b Uozumi Y. Kikuchi M. Synlett  2005,  1775 
  • 9c Yoshikawa S. Odaira J.-i. Kitamura Y. Bedekar AV. Furuta T. Tanaka K. Tetrahedron  2004,  60:  2225 
    Suche in Google Scholar
  • Reccent examples of other transition-metal reagents:
  • 10a Motomura T. Nakamura H. Suginome M. Murakami M. Ito Y. Bull. Chem. Soc. Jpn.  2005,  78:  142 
    Suche in Google Scholar
  • 10b Spivey AC. Zhu F. Mitchell MB. Davey SG. Jarvest RL. J. Org. Chem.  2003,  68:  7379 
    Suche in Google Scholar
  • Selected examples of nontransition-metal-catalyzed formation of bromobiaryls:
  • 11a Leyva A. Garcia H. Corma A. Tetrahedron  2007,  63:  7097 
    Suche in Google Scholar
  • 11b Leroux FR. Bonnafoux L. Heiss C. Colobert F. Lanfranchi DA. Adv. Synth. Catal.  2007,  349:  2705 
    Suche in Google Scholar
  • 11c Barder TE. Walker SD. Martinelli JR. Buchwald SL. J. Am. Chem. Soc.  2005,  127:  4685 
    Suche in Google Scholar
  • 11d Becht J.-M. Ngouela S. Wagner A. Mioskowski C. Tetrahedron  2004,  60:  6853 
    Suche in Google Scholar
  • 11e Leroux F. Schlosser M. Angew. Chem. Int. Ed.  2002,  41:  4272 
    Suche in Google Scholar
  • 12 Dong C.-G. Hu Q.-S. J. Am. Chem. Soc.  2005,  127:  10006 
    CrossrefPubMedSuche in Google Scholar
  • 13a For an example of using organometallic reagents to control the selectivity between Br group and OTf group for the formation of 2-bromobiaryls, see: Comins DL. O’Connor S. In Advances in Heterocyclic Chemistry   Vol. 44:  Katritzky AR. Academic Press; San Diego: 1988.  p.199-267  
    Suche in Google Scholar
  • For recent examples, see:
  • 13b Young DD. Deiters A. Angew. Chem. Int. Ed.  2007,  46:  5187 
    Suche in Google Scholar
  • 13c Karig G. Spencer JA. Gallagher T. Org. Lett.  2001,  3:  835 
    Suche in Google Scholar
  • For a recent example of selective transition-metal-catalyzed cross-coupling of 2,3-dihalopyridines, see:
  • 14a Handy ST. Wilson T. Muth A. J. Org. Chem.  2007,  72:  8496 
    Suche in Google Scholar
  • 14b Simkovsky NM. Ermann M. Roberts SM. Parry DM. Baxter D. J. Chem. Soc., Perkin Trans. 1  2002,  1847 
  • 14c Gauthier DR. Szumigala RH. Dormer PG. Armstrong JD. Volante RP. Reider PJ. Org. Lett.  2002,  4:  375 
    Suche in Google Scholar
  • 14d Kim C.-S. Russell KC. J. Org. Chem.  1998,  63:  8229 
    Suche in Google Scholar
  • 14e Quallich GJ. Fox DE. Friedmann RC. Murtiashaw CW. J. Org. Chem.  1992,  57:  761 
    Suche in Google Scholar
15

We have also tested Pd/C/Ph3P- and Pd(PPh3)4/Ph3P-catalyzed cross-coupling reactions of o-bromoiodobenzenes with arylboronic acids and found bromobiaryls were formed exclusively with excellent yields.