Download PDF
Synthesis 2008(10): 1575-1579  
DOI: 10.1055/s-2008-1072570
PAPER
© Georg Thieme Verlag Stuttgart · New York

Efficient Palladium-Catalyzed Synthesis of Aminopyridyl Phosphonates from Bromopyridines and Diethyl Phosphite

Alla Bessmertnykh, Christiane Morkos Douaihy, Sankar Muniappan, Roger Guilard*
Institut de Chimie Moléculaire, Université de Bourgogne (ICMUB) - UMR 5260 CNRS, 9, av. Alain Savary, 21078 Dijon, France
Fax: +33(3)80396138; e-Mail: Roger.Guilard@u-bourgogne.fr;
Further Information

Publication History

Received 15 January 2008
Publication Date:
27 March 2008 (online)

    Permissions and Reprints All articles of this category

Abstract

A general method for coupling aminopyridyl bromides with diethyl phosphite is reported. This efficient route is realized through the use of a palladium catalyst and triethylamine as base.

Key words

palladium - catalysis - phosphonates - cross-coupling - pyridyl halides

    References

  • For reviews, see:
  • 1a Muci AR. Buchwald SL. Top. Curr. Chem.  2002,  219:  131 
    CrossrefGoogle Scholar
  • 1b Hartwig JF. In Handbook of Organopalladium Chemistry for Organic Synthesis   Vol. 1:  Negishi E.-I. Wiley-Interscience; New York: 2002. 
    CrossrefGoogle Scholar
  • 1c Beletskaya IP. Pure Appl. Chem.  1997,  69:  471 
    CrossrefGoogle Scholar
  • 2a Hirao T. Masunaga T. Ohshiro Y. Agawa T. Synthesis  1981,  56 
    CrossrefGoogle Scholar
  • 2b Hirao T. Masunaga T. Yamada N. Ohshiro Y. Agawa T. Bull. Chem. Soc. Jpn.  1982,  55:  909 
    CrossrefGoogle Scholar
  • 2c Petrakis KS. Nagabhushan TL. J. Am. Chem. Soc.  1987,  109:  2831 
    CrossrefGoogle Scholar
  • 2d Kabachnik MM. Solntseva MD. Izmer VV. Novikova ZS. Beletskaya IP. Russ. J. Org. Chem.  1998,  34:  93 
    CrossrefGoogle Scholar
  • 2e Defacqz N. de Bueger B. Touillaux R. Cordi A. Marchand-Brynaert J. Synthesis  1999,  1368 
    CrossrefGoogle Scholar
  • 2f Ngo HL. Lin W. J. Am. Chem. Soc.  2002,  124:  14298 
    CrossrefGoogle Scholar
  • For Ni- or Cu-mediated coupling of aryl halides with trialkyl phosphites, see:
  • 3a Tavs P. Korte F. Tetrahedron  1967,  23:  4677 
    Google Scholar
  • 3b Tavs P. Chem. Ber.  1970,  103:  2428 
    Google Scholar
  • 3c Osuka A. Ohmasa N. Yoshida Y. Suzuki H. Synthesis  1983,  69 
    Google Scholar
  • 3d Yuan C. Feng H. Synthesis  1990,  140 
    Google Scholar
  • 3e Czech BP. Desai DH. Koszuk J. Czech A. Babb DA. Robison TW. Bartsch RA. J. Heterocycl. Chem.  1992,  29:  867 
    Google Scholar
  • 3f For Cu-promoted coupling of aryl halides with dialkyl phosphites, see: Ogawa T. Usuki N. Ono N. J. Chem. Soc., Perkin Trans. 1  1998,  2953 
    Google Scholar
  • 3g For Cu-catalyzed coupling of aryl iodides with dialkyl phosphites, see: Gelman D. Jiang L. Buchwald SL. Org. Lett.  2003,  5:  2315 
    Google Scholar
  • 3h For Cu-catalyzed reactions of diazonium salt with PCl3, see: Freedman LD. Doak GO. J. Am. Chem. Soc.  1955,  77:  173 
    Google Scholar
  • 3i For Friedel-Crafts reaction of arenes with phosphorous derivatives, see: Kosolapoff GM. J. Am. Chem. Soc.  1952,  74:  4119 
    Google Scholar
  • 3j For nucleophilic substitution reaction of activated aryl halides with sodium dialkylphosphites, see: Boumekouez A. About-Jaudet E. Savignac NCP. J. Organomet. Chem.  1992,  440:  297 
    Google Scholar
  • 3k For SRN1 substitution reaction of aryl halides with sodium dialkylphosphites, see: Beugelmans R. Chbani M. Bull. Soc. Chim. Fr.  1995,  132:  290 
    Google Scholar
  • 4a Johansson T. Stawinski J. Chem. Commun.  2001,  2564 
    Google Scholar
  • 4b Ayyappan P. Evans OR. Foxman BM. Wheeler KA. Warren TH. Lin W. Inorg. Chem.  2001,  40:  5954 
    Google Scholar
  • 4c Ayyappan P. Evans OR. Cui Y. Wheeler KA. Lin W. Inorg. Chem.  2002,  41:  4978 
    Google Scholar
  • 4d Ziessel RF. Charbonniere LJ. Mameri S. Camerel F. J. Org. Chem.  2005,  14:  9835 
    Google Scholar
  • 5 Bulot JJ. Aboujaoude EE. Collignon N. Savignac P. Phosphorus, Sulfur Relat. Elem.  1984,  21:  197 
    CrossrefGoogle Scholar
  • 6 Penicaud V. Odobel F. Bujoli B. Tetrahedron Lett.  1998,  39:  3689 
    CrossrefGoogle Scholar
  • 7a Yates FS. Pyridines and their Benzo Derivatives: (vi) Applications, In Comprehensive Heterocyclic Chemistry. The Structure, Reactions, Synthesis and Uses of Heterocyclic Compounds   Vol. 2:  Katritzky AR. Rees CW. Pergamon Press; Oxford: 1984. 
    Google Scholar
  • 7b Pyridine and its Derivatives   Part 5:  Newkome GR. Wiley-Interscience; New York: 1984. 
    Google Scholar
  • 7c The Merck Index: An Encyclopedia of Chemicals, Drugs and Biologicals   Merck Research Laboratories Division of Merck & CO., INC.; Whitehouse Station NJ: 2001. 
    Google Scholar
  • 8 Pierrat P. Gros PC. Fort Y. J. Comb. Chem.  2005,  7:  879 
    CrossrefGoogle Scholar
  • 9 Gooßen LJ. Dezfuli MK. Synlett  2005,  445 
    Article in Thieme ConnectGoogle Scholar