Download PDF
Synlett 2002(6): 0871-0874
DOI: 10.1055/s-2002-31930
LETTER
© Georg Thieme Verlag Stuttgart · New York

Palladium- or Nickel-Catalyzed Cross-Coupling of Organotitanium Reagents with Aryl Triflates and Halides

Jin Wook Han, Norihito Tokunaga, Tamio Hayashi*
Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606-8502, Japan
Fax: +81(75)7533988; e-Mail: thayashi@kuchem.kyoto-u.ac.jp;
Further Information

Publication History

Received 20 March 2002
Publication Date:
07 February 2007 (online)

    Permissions and Reprints All articles of this category

Abstract

The reaction of organotitanium reagents, methyltitanium triisopropoxide [MeTi(i-PrO)3] and phenyltitanium triisopropoxide [PhTi(i-PrO)3], with aryl triflates and halides proceeded in the presence of 1.0 mol% of palladium catalyst coordinated with (R*)-N,N-dimethyl-1-[(S*)-2-(diphenylphosphino)ferrocenyl]ethyl­amine [(R*)-(S*)-PPFA] in refluxing THF to give a quantitative yield of the corresponding cross-coupling products.

Key words

cross-coupling - organotitanium - palladium catalyst - aryl triflate - aryl halide

    References and Notes

  • For reviews:
  • 1a Metal-Catalyzed Cross-Coupling Reactions   Diederich F. Stang PJ. Wiley-VCH; Weinheim: 1998. 
    Google Scholar
  • 1b Geissler H. In Transition Metals for Organic Synthesis   Vol. 1:  Beller M. Bolm C. Wiley-VCH; Weinheim: 1998.  p.158 
    Google Scholar
  • 1c Tsuji J. Palladium Reagents and Catalysts   Wiley; Chichester: 1995.  p.125-290  
    Google Scholar
  • 2a Pérez I. Sestelo JP. Sarandeses LA. J. Am. Chem. Soc.  2001,  123:  4155 
    CrossrefGoogle Scholar
  • 2b Pérez I. Sestelo JP. Sarandeses LA. Org. Lett.  1999,  1:  1267 
    CrossrefGoogle Scholar
  • 3a Rao MLN. Yamazaki O. Shimada S. Tanaka T. Suzuki Y. Tanaka M. Org. Lett.  2001,  3:  4103 
    CrossrefGoogle Scholar
  • 3b Rao MLN. Shimada S. Tanaka M. Org. Lett.  1999,  1:  1271 
    CrossrefGoogle Scholar
  • For reviews:
  • 4a Duthaler RO. Hafner A. In Transition Metals for Organic Synthesis   Vol. 1:  Beller M. Bolm C. Wiley-VCH; Weinheim: 1998.  p.447 
    Google Scholar
  • 4b Reetz MT. Organotitanium Reagents in Organic Synthesis   Springer Verlag; Berlin: 1986. 
    Google Scholar
  • 5 For a pertinent review: Sato F. Urabe H. Okamoto S. Chem. Rev.  2000,  100:  2835 
    CrossrefGoogle Scholar
  • 6 Reetz MT. Westermann J. Steinbach R. Wenderoth B. Peter R. Ostarek R. Maus S. Chem. Ber.  1985,  118:  1421 
    CrossrefGoogle Scholar
  • 7 Weidmann B. Widler L. Olivero AG. Maycock CD. Seebach D. Helv. Chim. Acta  1981,  64:  357 
    CrossrefGoogle Scholar
  • Examples of transition metal-catalyzed reaction of organotitanium reagents:
  • 8a Nickel-catalyzed 1,4-addition: Flemming S. Kabbara J. Nickisch K. Neh H. Westermann J. Tetrahedron Lett.  1994,  35:  6075 
    Google Scholar
  • 8b Copper-catalyzed SN2′ allylation and conjugate addition: Arai M. Lipshutz BH. Nakamura E. Tetrahedron  1992,  48:  5709 
    Google Scholar
  • 8c Palladium-catalyzed allylic alkylation: Kasatkin AN. Kulak AN. Tolstikov GA. Lomakina SI. Izv. Akad. Nauk, Ser. Khim.  1988,  2159 ; Chem. Abstr. 1989, 110, 231227
    Google Scholar
  • 8d See also: Kasatkin AN. Kulak AN. Tolstikov GA. Izv. Akad. Nauk, Ser. Khim.  1987,  391 ; Chem. Abstr. 1988, 108, 38014
    Google Scholar
  • 9 Hayashi T. Mise T. Fukushima M. Kagotani M. Nagashima N. Hamada Y. Matsumoto A. Kawakani S. Konishi M. Yamamoto K. Kumada M. Bull. Chem. Soc. Jpn.  1980,  53:  1138 
    Google Scholar
  • 10 Hayashi T. Tajika M. Tamao K. Kumada M. J. Am. Chem. Soc.  1976,  98:  3718 
    CrossrefGoogle Scholar
  • 11 Ogasawara M. Yoshida K. Hayashi T. Organometallics  2000,  19:  1567 
    CrossrefGoogle Scholar
  • 12 Mikami K. Terada M. Nakai T. J. Am. Chem. Soc.  1990,  112:  3949 
    CrossrefGoogle Scholar