Download PDF
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;
Further Information

Publication History

Received 13 December 2011
Publication Date:
14 February 2012 (online)

    Permissions and Reprints All articles of this category

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

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