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Synlett 2012(3): 463-467  
DOI: 10.1055/s-0031-1290320
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Palladium-Catalyzed Regioselective Arylation of Arene C-H Bond Assisted by the Removable 2-Pyridylsulfinyl Group

Xunbin Zhanga, Ming Yua, Jinzhong Yaoa, Yuhong Zhang*a,b
a Department of Chemistry, Zhejiang University, Hangzhou 310027, P. R. of China
Fax: +86(571)87953244; e-Mail: yhzhang@zju.edu.cn;
b State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, P. R. of China
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Publikationsverlauf

Received 26 October 2011
Publikationsdatum:
25. Januar 2012 (online)

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Abstract

A palladium-catalyzed arylation of arene C-H bond assisted by a removable 2-pyridylsulfinyl group is described. The reaction employs aryltrifluoroborates as the arylation reagent, leading to the corresponding products in moderate to good yield with broad substrate scope. The directing group can be removed or converted to other useful functionalities, which showcases the potential synthetic application of the methodology.

Key words

C-H bond activation - arylation - aryltrifluoroborate - sulfoxide - palladium catalysis

    References

  • For selected reviews, see:
  • 1a Miyaura N. Suzuki A. Chem. Rev.  1995,  95:  2457 
    Suche in Google Scholar
  • 1b Littke AF. Fu GC. Angew. Chem. Int. Ed.  2002,  41:  4176 
    Suche in Google Scholar
  • 1c Hassan J. Sevignon M. Gozzi C. Schulz E. Lemaire M. Chem. Rev.  2002,  102:  1359 
    Suche in Google Scholar
  • 1d Christmann U. Vilar R. Angew. Chem. Int. Ed.  2005,  44:  366 
    Suche in Google Scholar
  • 1e Wu X.-F. Anbarasan P. Neumann H. Beller M. Angew. Chem. Int. Ed.  2010,  49:  9047 
    Suche in Google Scholar
  • For selected general reviews of transition-metal-catalyzed C-H arylation, see:
  • 2a Campeau LC. Fagnou K. Chem. Commun.  2006,  1253 
  • 2b Yu J.-Q. Giri R. Chen X. Org. Biomol. Chem.  2006,  4:  4041 
    Suche in Google Scholar
  • 2c Godula K. Sames D. Science  2006,  312:  67 
    Suche in Google Scholar
  • 2d Alberico D. Scott ME. Lautens M. Chem. Rev.  2007,  107:  174 
    Suche in Google Scholar
  • 2e Beccalli EM. Broggini G. Martinelli M. Sottocornola S. Chem. Rev.  2007,  107:  5318 
    Suche in Google Scholar
  • 3 For recent review of ligand-directed activation reactions, see: Lyons TW. Sanford MS. Chem. Rev.  2010,  110:  1147 
    Suche in Google Scholar
  • 4a Oi S. Fukita S. Inoue Y. Chem. Commun.  1998,  2439 
  • 4b Cheng K. Yao B. Zhao J. Zhang Y. Org. Lett.  2008,  10:  5309 
    Suche in Google Scholar
  • 4c Deprez NR. Sanford MS. J. Am. Chem. Soc.  2009,  131:  11234 
    Suche in Google Scholar
  • 4d Wang X. Truesdale L. Yu J.-Q. J. Am. Chem. Soc.  2010,  132:  3648 
    Suche in Google Scholar
  • 4e Shuai Q. Yang L. Guo X. Baslé O. Li C.-J. J. Am. Chem. Soc.  2010,  132:  12212 
    Suche in Google Scholar
  • 4f Li W. Yin Z. Jiang X. Sun P. J. Org. Chem.  2011,  76:  8543 
    Suche in Google Scholar
  • 5a Pastine SJ. Gribkov DV. Sames D. J. Am. Chem. Soc.  2006,  128:  14220 
    Suche in Google Scholar
  • 5b Tredwell MJ. Gulias M. Gaunt Bremeyer N. Johansson CCC. Collins BSL. Gaunt MJ. Angew. Chem. Int. Ed.  2011,  50:  1076 
    Suche in Google Scholar
  • 6 Sun C.-L. Liu N. Li B.-J. Yu D.-G. Wang Y. Shi Z.-J. Org. Lett.  2010,  12:  184 
    Suche in Google Scholar
  • 7a Giri R. Maugel N. Li J.-J. Wang D.-H. Breazzano SP. Saunders LB. Yu J.-Q. J. Am. Chem. Soc.  2007,  129:  3510 
    Suche in Google Scholar
  • 7b Wang D.-H. Mei T.-S. Yu J.-Q. J. Am. Chem. Soc.  2008,  130:  17676 
    Suche in Google Scholar
  • 7c Engle KM. Thuy-Boun PS. Dang M. Yu J.-Q. J. Am. Chem. Soc.  2011,  133:  18183 
    Suche in Google Scholar
  • 8 Shi Z. Li B. Wan X. Cheng J. Fang Z. Cao B. Qin C. Wang Y. Angew. Chem. Int. Ed.  2007,  46:  5554 
    Suche in Google Scholar
  • 9 Nishikata T. Abela AR. Huang S. Lipshutz BH.
    J. Am. Chem. Soc.  2010,  132:  4978 
    Suche in Google Scholar
  • 10a Chernyak N. Dudnik AS. Huang C. Gevorgyan V. J. Am. Chem. Soc.  2010,  132:  8270 
    Suche in Google Scholar
  • 10b Dudnik AS. Chernyak N. Huang C. Gevorgyan V. Angew. Chem. Int. Ed.  2010,  49:  8729 
    Suche in Google Scholar
  • 11a García-Rubia A. Fernández-Ibáñez MA. Arrayás RG. Carretero JC. Chem. Eur. J.  2011,  17:  3567 
    Suche in Google Scholar
  • 11b Richter H. Beckendorf S. Mancheño OG. Adv. Synth. Catal.  2011,  353:  295 
    Suche in Google Scholar
  • 11c Yu M. Liang Z. Wang Y. Zhang Y. J. Org. Chem.  2011,  76:  4987 
    Suche in Google Scholar
  • For the use of the related (2-pyridyl)sulfonyl group in C-H functionalization of nitrogen-containing arenes and heteroarenes, see:
  • 11d García-Rubia A. Arrayás RG. Carretero JC. Angew. Chem. Int. Ed.  2009,  48:  6511 
    Suche in Google Scholar
  • 11e García-Rubia A. Urones B. Gómez Arrayás R. Carretero JC. Chem. Eur. J.  2010,  16:  9676 
    Suche in Google Scholar
  • 11f García-Rubia A. Urones B. Gómez Arrayás R. Carretero JC. Angew. Chem. Int. Ed.  2011,  50:  10927 
    Suche in Google Scholar
  • 12a Molander GA. Fumagalli T. J. Org. Chem.  2006,  71:  5743 
    Suche in Google Scholar
  • 12b Molander GA. Brown AR. J. Org. Chem.  2006,  71:  9681 
    Suche in Google Scholar
  • 12c Molander GA. Jean-Gerard L. J. Org. Chem.  2007,  72:  8422 
    Suche in Google Scholar
  • 12d Molander GA. Petrillo DE. Org. Lett.  2008,  10:  1795 
    Suche in Google Scholar
  • 12e Molander GA. Gormisky PE. Sandrock DL. J. Org. Chem.  2008,  73:  2052 
    Suche in Google Scholar
  • 12f Zhao J. Zhang Y. Cheng K. J. Org. Chem.  2008,  73:  7428 
    Suche in Google Scholar
  • 13a Chen X. Li J.-J. Hao X.-S. Goodhue CE. Yu J.-Q. J. Am. Chem. Soc.  2006,  128:  78 
    Suche in Google Scholar
  • 13b Chen X. Goodhue CE. Yu J.-Q. J. Am. Chem. Soc.  2006,  128:  12634 
    Suche in Google Scholar
  • 13c Hull KL. Sanford MS. J. Am. Chem. Soc.  2009,  131:  9651 
    Suche in Google Scholar
  • 14a Hassan J. Sevignon M. Gozzi C. Lemaire M. Chem. Rev.  2002,  102:  1359 
    Suche in Google Scholar
  • 14b Moreno-Mañas M. Pérez M. Pleixats R. J. Org. Chem.  1996,  61:  2346 
    Suche in Google Scholar
  • 14c Aramendia MA. Lafont F. Moreno-Mañnas M. Pleixats R. Roglans A. J. Org. Chem.  1999,  64:  3592 
    Suche in Google Scholar
  • 15a Furukawa N. Ogawa S. Matsumura K. Fujihara H. J. Org. Chem.  1991,  56:  6341 
    Suche in Google Scholar
  • 15b García Ruano JL. Fernández-Ibáñez M. Maestro MC. Rodríguez-Fernández MM. J. Org. Chem.  2005,  70:  1796 
    Suche in Google Scholar