Synthesis 2012(7): 1043-1050  
DOI: 10.1055/s-0031-1289748
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Manganese(III) Acetate Mediated Free-Radical Phosphonylation of Flavones and Coumarins

Peng Zhoua, Yao-Jia Jianga, Jian-Ping Zou*a, Wei Zhang*b
a Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry and Chemical Engineering, Suzhou University, 199 Renai Street, Suzhou, Jiangsu 215123, P. R. of China
Fax: +86(512)65880335; e-Mail: jpzou@suda.edu.cn;
b Department of Chemistry, University of Massachusetts Boston, 100 Morrissey Boulevard, Boston, MA 02125, USA
Fax: +1(617)2876030; e-Mail: wei2.zhang@umb.edu;
Further Information

Publication History

Received 29 December 2011
Publication Date:
14 March 2012 (online)

Abstract

The phosphonyl radical generated from the reaction of manganese(III) acetate with diethyl phosphonate selectively adds to the 3-position of flavones and coumarins to afford phosphonylated products in moderate to good yields.

    References

  • Reviews on P-centered radicals:
  • 1a Leca D. Fensterbank L. Lacote E. Malacria M. Chem. Soc. Rev.  2005,  34:  858 
  • 1b Marque S. Tordo P. Top. Curr. Chem.  2005,  250:  43 
  • 2 Kagayama T. Nakano A. Sakaguchi S. Ishii Y. Org. Lett.  2006,  8:  407 
  • 3 Xu W. Zou J.-P. Zhang W. Tetrahedron Lett.  2010,  51:  2639 
  • 4 Mu X.-J. Zou J.-P. Qian Q.-F. Zhang W. Org. Lett.  2006,  8:  5291 
  • 5 Pan X.-Q. Zou J.-P. Zhang G.-L. Zhang W. Chem. Commun.  2010,  46:  1721 
  • 6 Zhou J. Zhang G.-L. Zou J.-P. Zhang W. Eur. J. Org. Chem.  2011,  3412 
  • 7 Pan X.-Q. Wang L. Zou J.-P. Zhang W. Chem. Commun.  2011,  47:  7875 
  • 8a Chu H.-W. Wu H.-T. Lee Y.-J. Tetrahedron  2004,  60:  2647 
  • 8b Chen IL. Chen JY. Shieh PC. Chen JJ. Lee CH. Juang SH. Wang TC. Bioorg. Med. Chem.  2008,  16:  7639 
  • 8c Harborne JB. Williams CA. Phytochemistry  2000,  55:  481 
  • 8d Murray RDH. Mendey J. Brown SA. In The Natural Coumarins   John Wiley & Sons; New York: 1982. 
  • 9 Engel R. In Handbook of Organophosphorus Chemistry   M. Dekker Inc.; New York: 1992. 
  • 10a Budzisz E. Nawrot E. Malecka M. Arch. Pharm. Pharm. Med. Chem.  2001,  334:  381 
  • 10b Budzisz E. Brzezinska E. Krajewska U. Rozalski M. Eur. J. Med. Chem.  2003,  38:  597 
  • 11 Van der Jeught S. Stevens CV. Chem. Rev.  2009,  109:  2672 
  • 12a Takeuchi Y. Ueda N. Uesugi K. Abe H. Nishioka H. Harayama T. Heterocycles  2003,  59:  217 
  • 12b Bojilova A. Nikolova R. Ivanov C. Rodios NA. Terzis A. Raptopoulou CP. Tetrahedron  1996,  52:  12597 
  • 12c Rodios NA. Bojilova A. Terzis A. Raptopoulou CP. J. Heterocycl. Chem.  1994,  31:  1129 
  • 12d Bouyssou P. Chenault J. Tetrahedron Lett.  1991,  32:  5341 
  • 12e Singh RK. Rogers MD. J. Heterocycl. Chem.  1985,  22:  1713 
  • 12f Robison CN. Addison JF. J. Org. Chem.  1966,  31:  4325 
  • 13a Budzisz E. Graczyk-Wojciechowska J. Ziebab R. Nawrot B. New J. Chem.  2002,  26:  1799 
  • 13b Kostka K. Pastuszko S. Porada M. Phosphorus, Sulfur Silicon Relat. Elem.  1992,  71:  67