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Synthesis 2012(6): 941-945  
DOI: 10.1055/s-0031-1289700
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Direct Oxidative C-P Bond Formation of Indoles with Dialkyl Phosphites

Haolong Wang, Xincheng Li, Fan Wu, Boshun Wan*
Dalian Institute of Chemical Physics, Chinese Academy of Sciences, 457 Zhongshan Road, Dalian 116023, P. R. of China
Fax: +86(411)84379223; e-Mail: bswan@dicp.ac.cn;
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Publikationsverlauf

Received 13 December 2011
Publikationsdatum:
14. Februar 2012 (online)

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Abstract

The direct phosphonation of indoles was developed. In this reaction, dialkyl phosphites and indoles were used as substrates, and the C-P bond was formed through oxidative coupling mediated by silver(I) acetate. Various indoles and different dialkyl phosphites were effective substrates for the reaction, and dialkylphosphoryl-substituted indoles were obtained in up to 71% yield.

Key words

indole - dialkyl phosphite - phosphonation - silver acetate - oxidative coupling

    References

  • 1a Organic Phosphorus Compounds   Kosolapoff GM. Maier L. Wiley-Interscience; New York: 1976. 
  • 1b Phosphorus: An Outline of Its Chemistry, Biochemistry and Uses   5th ed.:  Corbridge DEC. Elsevier; Amsterdam: 1995. 
  • 1c The Chemistry of Organophosphorus Compounds   Vol. 4:  Hartley FR. Wiley; New York: 1996. 
  • 2 Michaelis A. Kaehne R. Ber. Dtsch. Chem. Ges.  1898,  31:  1048 
    Suche in Google Scholar
  • 3 Hirao T. Masunaga T. Ohshiro Y. Agawa T. Synthesis  1981,  5 
  • 4a Schwan AL. Chem. Soc. Rev.  2004,  33:  218 
    Suche in Google Scholar
  • 4b Tappe FMJ. Trepohl VT. Oestreich M. Synthesis  2010,  3037 
  • 4c Rao H. Jin Y. Fu H. Zhao Y. Chem. Eur. J.  2006,  12:  3636 
    Suche in Google Scholar
  • 4d Tappe FMJ. Trepohl VT. Oestreich M. Synthesis  2010,  3037 
  • 4e Beletskaya IP. Kazankova MA. Russ. J. Org. Chem.  2002,  38:  1391 
    Suche in Google Scholar
  • 5a Andaloussi M. Lindh J. Savmarker J. Sjoberg PJR. Larhed M. Chem. Eur. J.  2009,  15:  13069 
    Suche in Google Scholar
  • 5b Zhuang R. Xu J. Fang M. Zhao Y. Org. Lett.  2011,  13:  2110 
    Suche in Google Scholar
  • 6a Jason EF. Fields EK. J. Org. Chem.  1962,  27:  1402 
    Suche in Google Scholar
  • 6b Kottman H. Skarzewski J. Effenberger F. Synthesis  1987,  797 
  • 6c Effenberger F. Kottmann H. Tetrahedron  1985,  41:  4171 
    Suche in Google Scholar
  • 6d Xu W. Zou J.-P. Zhang W. Tetrahedron Lett.  2010,  51:  2639 
    Suche in Google Scholar
  • 7a Tayama O. Nakano A. Iwahama T. Sakaguchi S. Ishii Y. J. Org. Chem.  2004,  69:  5494 
    Suche in Google Scholar
  • 7b Kagayama T. Nakano A. Sakaguchi S. Ishii Y. Org. Lett.  2006,  8:  407 
    Suche in Google Scholar
  • 8 Mu X.-J. Zou J.-P. Qian Q.-F. Zhang W. Org. Lett.  2006,  8:  5291 
    Suche in Google Scholar
  • 9a Razumor AI. Gurevich PA. J. Gen. Chem. USSR (Engl. Transl.)  1967,  37:  1532 
    Suche in Google Scholar
  • 9b Haelters JP. Corbel B. Sturtz G. Phosphorus, Sulfur, Silicon, Relat. Elem.  1988,  37:  65 
    Suche in Google Scholar
  • 9c Jiao X.-Y. Xiong F.-G. Chen W.-Y. Hu B.-F. Chin. J. Org. Chem.  1994,  14:  622 
    Suche in Google Scholar
  • 10 Thielges S. Meddah E. Bisseret P. Eustache J. Tetrahedron Lett.  2004,  45:  907 
    Suche in Google Scholar
  • 12a Cho SH. Kim JY. Lee SY. Chang S. Angew. Chem. Int. Ed.  2009,  48:  9127 
    Suche in Google Scholar
  • 12b Wang D.-S. Chen Q.-A. Zhou Y.-G. Zhang X.-M. J. Am. Chem. Soc.  2010,  132:  8909 
    Suche in Google Scholar
11

The influence of metals and acids were tested and listed in the Supporting Information.