PDF icon PDF herunterladen
Synlett 2011(7): 923-926  
DOI: 10.1055/s-0030-1259726
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

meta-Selective Substitution of Phenols with Indoles via One-Pot Oxidative Dearomatization-Michael Addition-Aromatization

Yang Yea, Hua Wanga, Renhua Fan*a,b
a Department of Chemistry, Fudan University, 220 Handan Road, Shanghai 200433, P. R. of China
Fax: +86(21)65642019; e-Mail: rhfan@fudan.edu.cn;
b Shanghai Key Laboratory of Molecular Catalysts and Innovative Materials, Department of Chemistry, Fudan University, 220 Handan Road, Shanghai 200433, P. R. of China
Weitere Informationen

Publikationsverlauf

Received 3 December 2010
Publikationsdatum:
10. März 2011 (online)

   Lizenzen und Reprints Alle Artikel dieser Rubrik
Preview

Abstract

An oxidative coupling strategy involving hypervalent organoiodine-induced oxidative dearomatization of 4-substituted phenols, Brønsted acid catalyzed Michael addition with indoles, and aromatization has been developed. The one-pot reaction provides an efficient access to the meta-indole-substituted phenol derivatives.

Key words

aromatic substitution - biaryls - cross-coupling reaction - oxidation - regioselectivity

    References

  • 1a Driver TG. Angew. Chem. Int. Ed.  2009,  48:  7974 
    Suche in Google Scholar
  • 1b Suárez-Pantiga S. Palomas D. Rubio E. Gonzalez JM. Angew. Chem. Int. Ed.  2009,  48:  7857 
    Suche in Google Scholar
  • 1c Cahiez G. Foulgoc L. Moyeux A. Angew. Chem. Int. Ed.  2009,  48:  2969 
    Suche in Google Scholar
  • 1d Seregin IV. Gevorgyan V. Chem. Soc. Rev.  2007,  36:  1173 
    Suche in Google Scholar
  • 1e Hiroaki O. Mio Y. Mutsumi I. Tetsuaki T. Angew. Chem. Int. Ed.  2005,  44:  5103 
    Suche in Google Scholar
  • 2a Zhou Y. Zhao L. Liu L. Angew. Chem. Int. Ed.  2009,  48:  7126 
    Suche in Google Scholar
  • 2b Park J.-W. Jun C.-H. ChemCatChem  2009,  1:  69 
    Suche in Google Scholar
  • For selected reviews, see:
  • 3a Moriarty RM. Vaid RK. Synthesis  1990,  431 
  • 3b Stang PJ. Zhdankin VV. Chem. Rev.  1996,  96:  1123 
    Suche in Google Scholar
  • 3c Zhdankin VV. Stang PJ. Chemistry of Hypervalent Compounds   Akiba K. VCH Publishers; New York: 1999.  Chap. 11. p.327 
  • 3d Grushin VV. Chem. Soc. Rev.  2000,  29:  315 
    Suche in Google Scholar
  • 3e Zhdankin VV. Stang PJ. Chem. Rev.  2002,  102:  2523 
    Suche in Google Scholar
  • 3f Stang PJ. J. Org. Chem.  2003,  68:  2997 
    Suche in Google Scholar
  • 3g Moriarty RM. J. Org. Chem.  2005,  70:  2893 
    Suche in Google Scholar
  • 3h Zhdankin VV. Stang PJ. Chem. Rev.  2008,  108:  5299 
    Suche in Google Scholar
  • For reviews of dearomatization methods, see:
  • 4a Bach T. Angew. Chem., Int. Ed. Engl.  1996,  35:  729 
    Suche in Google Scholar
  • 4b Rabideau PW. Marcinow Z. Org. React.  1992,  42:  1 
    Suche in Google Scholar
  • 4c Cornelisse J. Chem. Rev.  1993,  93:  615 
    Suche in Google Scholar
  • 4d For a recent examples of dearomatization methods, see: Clayden J. Dufour J. Grainger DM. Helliwell M. J. Am. Chem. Soc.  2007,  129:  7488 
    Suche in Google Scholar
  • 4e Clayden J. Total Synthesis of Kanoids by Dearomatizing Anionic Cyclization, In Strategies and Tactics in Organic Synthesis   Vol. 4:  Harmata M. Academic Press; London: 2004.  p.72 
    Suche in Google Scholar
  • 4f Vo NT. Pace RDM. O’Hara F. Gaunt MJ. J. Am. Chem. Soc.  2008,  130:  404 
    Suche in Google Scholar
  • For selected examples of oxidative dearomatization in synthesis, see:
  • 5a Gagnepain J. Castet F. Quideau S. Angew. Chem. Int. Ed.  2007,  46:  1533 
    Suche in Google Scholar
  • 5b Cook SP. Polara A. Danishefsky SJ. J. Am. Chem. Soc.  2006,  128:  16440 
    Suche in Google Scholar
  • 5c Mejorado LH. Pettus TRR. J. Am. Chem. Soc.  2006,  128:  15625 
    Suche in Google Scholar
  • 5d Scheffler G. Seike H. Sorensen EJ. Angew. Chem. Int. Ed.  2000,  39:  4593 
    Suche in Google Scholar
  • 5e Berube A. Drutu I. Wood JL. Org. Lett.  2006,  8:  5421 
    Suche in Google Scholar
  • 5f Zhu J. Porco JA. Org. Lett.  2006,  8:  5169 
    Suche in Google Scholar
  • 6a Colletti SL. Li C. Fisher MH. Wyvratt MJ. Meinke PT. Tetrahedron Lett.  2000,  41:  7825 
    Suche in Google Scholar
  • 6b Chu L. Hutchins JE. Weber AE. Lo J.-L. Yang YT. Cheng K. Smith RG. Fisher MH. Wyvratt MJ. Goulet MT. Bioorg. Med. Chem. Lett.  2001,  11:  509 
    Suche in Google Scholar
  • 6c Stevenson GI. Smith AL. Lewis S. Michie SG. Neduvelil JG. Patel S. Marwood R. Patel S. Castro JL. Bioorg. Med. Chem. Lett.  2000,  10:  2697 
    Suche in Google Scholar
  • 7a Dipakranjan M. Pallab P. Bidyut KS. Tetrahedron Lett.  2005,  46:  2097 
    Suche in Google Scholar
  • 7b Ohkata K. Tamura Y. Shetuni BB. Takagi R. Miyanaga W. Kojima S. Paquette LA. J. Am. Chem. Soc.  2004,  126:  16783 
    Suche in Google Scholar