Synthesis 2009(18): 3094-3098  
DOI: 10.1055/s-0029-1216942
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Suzuki Coupling of Heteroaromatic Chlorides Using Highly Electron-Donating ClickPhos Ligands

Stephen M. Spinella, Zheng-Hui Guan, Jian Chen, Xumu Zhang*
Department of Chemistry and Chemical Biology & Department of Pharmaceutical Chemistry, Rutgers the State University of New Jersey, 160 Frelinghuysen Rd, Piscataway, NJ 08854, USA
Fax: +1(732)4456312; e-Mail: xumu@rutgers.edu;
Further Information

Publication History

Received 18 March 2009
Publication Date:
14 August 2009 (online)

Abstract

Using highly electron-rich monophosphine ligands, Suzuki­ cross-coupling of heteroaromatic chlorides with various boronic­ acids was carried out in high yields. High yields were also often observed when steric heteroaromatic chlorides were employed in Suzuki cross-coupling reactions.

    References

  • 1a Miyaura N. Suzuki A. Chem. Rev.  1996,  95:  2457 
  • 1b Littke AF. Fu GC. Angew. Chem. Int. Ed.  2002,  41:  1290 
  • 1c Miyaura N. Suzuki A. Chem. Rev.  1995,  95:  2457 
  • 1d Diederich F. Stang PJ. Metal-Catalyzed Cross-Coupling Reactions   Wiley-VCH; Weinheim: 1998. 
  • 1e de Meijere A. Diederich F. Metal-Catalyzed Cross-Coupling Reactions   Wiley-VCH; Weinheim: 2004. 
  • 2a Dehmel F. Molander GA. J. Am. Chem. Soc.  2004,  33:  10313 
  • 2b Durham TB. Blanchard N. Savall B. Noel A. Roush WR. J. Am. Chem. Soc.  2006,  126:  9307 
  • 3a Christmann U. Vilar R. Angew. Chem. Int. Ed.  2005,  44:  366 
  • 3b Miura M. Angew. Chem. Int. Ed.  2004,  43:  2201 
  • 4a Littke AF. Fu GC. Angew. Chem. Int. Ed.  2002,  41:  4176 
  • 4b Barder TE. Walker SD. Martinelli JR. Buchwald SL. J. Am. Chem. Soc.  2005,  127:  4685 
  • 5a Littke AF. Dai C. Fu GC. J. Am. Chem. Soc.  2000,  124:  4020 
  • 5b Netherton MR. Dai C. Neuschutz K. Fu GC. J. Am. Chem. Soc.  2001,  123:  10099 
  • 5c Kirchhoff JH. Netherton MR. Hills ID. Fu GC. J. Am. Chem. Soc.  2002,  124:  13662 
  • 5d Kudo N. Perseghini M. Fu GC. Angew. Chem. Int. Ed.  2006,  45:  1282 
  • 6a Wolfe JP. Tomori H. Sadighi JP. Yin J. Buchwald SL. J. Org. Chem.  2000,  65:  1158 
  • 6b Yin J. Rainka MP. Zhang X. Buchwald SL. J. Am. Chem. Soc.  2002,  124:  1162 
  • 6c Nguyen HN. Huang X. Buchwald SL. J. Am. Chem. Soc.  2003,  125:  11818 
  • 6d Walker SD. Barder TE. Martinelli JR. Buchwald SL. Angew. Chem. Int. Ed.  2004,  43:  1871 
  • 6e Barder TE. Walker SD. Martinelli JR. Buchwald SL. J. Am. Chem. Soc.  2005,  127:  4685 
  • 6f Billingsley KL. Anderson KW. Buchwald SL. Angew. Chem. Int. Ed.  2006,  45:  3484 
  • 6g Billingsley K. Buchwald SL. J. Am. Chem. Soc.  2007,  129:  3358 
  • 7a Stambuli JP. Kuwano R. Hartwig JF. Angew. Chem. Int. Ed.  2002,  41:  4746 
  • 7b Kataoka N. Shelby Q. Stambuli JP. Hartwig JF. J. Org. Chem.  2002,  67:  5553 
  • 8a Zapf A. Jackstell R. Rataboul F. Reirmeier T. Monsees A. Fuhrmann C. Shaikh N. Dingerdissen U. Beller M. Chem. Commun.  2004,  38 
  • 8b Harkal S. Rataboul F. Zapf A. Fuhrmann C. Reirmeier T. Monsees A. Beller M. Adv. Synth. Catal.  2004,  346:  1742 
  • 8c For a review, see: Zapf A. Beller M. Chem. Commun.  2005,  431 
  • 9a Dai Q. Gao W. Liu D. Zhang X. Org. Lett.  2005,  7:  4907 
  • 9b Dai D. Gao W. Liu D. Kapes LM. Zhang X. J. Org. Chem.  2006,  71:  3928 
  • 10a Kudo N. Perseghini M. Fu GC. Angew. Chem. Int. Ed.  2006,  45:  1282 
  • 10b Billingsley KL. Anderson KW. Buchwald SL. Angew. Chem. Int. Ed.  2006,  45:  3484 
  • 10c Guram AS. King AO. Allen JG. Wang X. Schenkel LB. Chan J. Bunel EE. Faul MM. Larsen RD. Martinelli MJ. Reider PJ. Org. Lett.  2006,  8:  1787 
  • 10d Billingsley K. Buchwald SL. J. Am. Chem. Soc.  2007,  129:  3358 
  • 10e Yamamoto Y. Takizawa M. Yu XQ. Miyaura N. Angew. Chem. Int. Ed.  2008,  47:  928