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Synthesis 2007(16): 2534-2538  
DOI: 10.1055/s-2007-983784
PAPER
© Georg Thieme Verlag Stuttgart · New York

Catalytic Sandmeyer Bromination

Irina P. Beletskaya*a, Alexander S. Sigeeva, Alexander S. Peregudovb, Pavel V. Petrovskiib
a Department of Chemistry, M. V. Lomonosov Moscow State University, 119992 Moscow, Russian Federation
b A. N. Nesmeyanov Institute of Organo-Element compounds, Russian Academy of Science, Vavilova str. 28, 119991 Moscow, Russian Federation
Fax: +7(495)9381844; e-Mail: Beletska@org.chem.msu.ru;
Further Information

Publication History

Received 10 May 2007
Publication Date:
12 July 2007 (online)

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Abstract

An efficient catalyst system for Sandmeyer bromination is proposed. Aryl bromides and dibromides can be obtained with excellent yield by this synthetic protocol.

Key words

catalysis - copper - diazo compounds - Sandmeyer reaction - halogenation

    References

  • 1 Handbook of Organopalladium Chemistry for Organic Synthesis   Negishi E. Wiley-Interscience; New York: 2002. 
    Google Scholar
  • 2a Suzuki A. In Metal-Catalyzed Cross-Coupling Reactions   de Meijere A. Diederich F. Wiley-VCH; Weinheim: 2004. 
    Google Scholar
  • 2b Hartwig JF. In Comprehensive Coordination Chemistry II   Vol. 9:  McCleverty JA. Meyer T. Elsevier; Amsterdam: 2004.  p.369 
    Google Scholar
  • 3 Heck RF. Palladium Reagents in Organic Synthesis   Academic Press; London: 1985. 
    Google Scholar
  • 4 Evans DA. Katz JL. Peterson GS. Hintermann T. J. Am. Chem. Soc.  2001,  123:  12411 
    CrossrefPubMedGoogle Scholar
  • 5 Beletskaya IP. Cheprakov AV. Coord. Chem. Rev.  2004,  248:  2337 
    CrossrefGoogle Scholar
  • 6a de la Mare PDB. Electrophilic Halogenation   Cambridge University Press; New York: 1976. 
    Google Scholar
  • 6b Snieckus V. Chem. Rev.  1990,  90:  879 
    Google Scholar
  • 7 Hodgson HH. Chem. Rev.  1947,  40:  251 
    CrossrefPubMedGoogle Scholar
  • 8 Beletskaya IP. Sigeev AS. Peregudov AS. Petrovskii PV. J. Organomet. Chem.  2004,  689:  3810 
    CrossrefGoogle Scholar
  • 9 Beletskaya IP. Sigeev AS. Peregudov AS. Petrovskii PV. Mendeleev Commun.  2006,  250 
    CrossrefGoogle Scholar
  • 10 Raznikiewicz T. Ark. Kemi  1963/1964,  301 ; Chem. Abstr. 1965, 59, 11317c
    Google Scholar
  • 11 Kravtsov DN. Kvasov BA. Khazanova TS. Fedin EI. J. Organomet. Chem.  1973,  61:  207 
    CrossrefGoogle Scholar
  • 12 Gorelik MV. Lomzakova VI. Khamidova EV. Shteiman VY. Kuznetsova MG. Andrievski AM. Russ. J. Org. Chem.  1995,  31:  508 
    Google Scholar
  • 13 Mirarchi D. Ritchie GLD. Aust. J. Chem.  1981,  34:  1443 
    CrossrefGoogle Scholar
  • 14 Buncel E. Manderviller RA. Dust JM. J. Chem. Soc., Perkin Trans. 2  1997,  1019 
    CrossrefGoogle Scholar
  • 15 Klusmer PAA. Hanekamp JC. Brandsma L. Schleyer PvR. J. Org. Chem.  1990,  55:  1311 
    CrossrefGoogle Scholar