Download PDF
Synthesis 2004(13): 2186-2190  
DOI: 10.1055/s-2004-829178
PAPER
© Georg Thieme Verlag Stuttgart · New York

An Improved Catalytic System, Pd(PPh3)4/PhCOOH Combined Catalyst, for the Allylation of Carbon Pronucleophiles with Allenes

Nitin T. Patil, Nirmal K. Pahadi, Yoshinori Yamamoto*
Department of Chemistry, Graduate School of Science, Tohoku University, Sendai 980-8578, Japan
e-Mail: yoshi@yamamoto1.chem.tohoku.ac.jp;
Further Information

Publication History

Received 21 April 2004
Publication Date:
27 July 2004 (online)

    Permissions and Reprints All articles of this category

Abstract

The reaction of allenes with active methynes and methylenes proceeded smoothly in the presence of Pd(PPh3)4/PhCOOH combined catalyst to give the corresponding monoallylated products with E-stereoselectivity in good to high yields. This result is in marked contrast to the previous finding that the reaction of allenes with active methynes, in the presence of Pd2(dba)3·CHCl3/dppb catalyst, affords the allylation products in lower yield with lower stereoselectivities.

Key words

palladium - carboxylic acids - catalysis - allenes - C-nucleophiles

    References

  • 1a Takahashi K. Miyake A. Hata G. Bull. Chem. Soc. Jpn.  1972,  45:  1183 
    Google Scholar
  • 1b Andell OS. Backvall J.-E. Moberg C. Acta. Chem. Scand. Ser. B  1986,  40:  184 
    Google Scholar
  • 1c Jolly PW. Kokel N. Synthesis  1990,  770 
    Google Scholar
  • 1d Mercier C. Miginani G. Aufrand N. Allmang G. Tetrahedron Lett.  1991,  32:  1433 
    Google Scholar
  • 1e Trost BM. Zhi L. Tetrahedron Lett.  1992,  33:  1381 
    Google Scholar
  • 2 Kadota I. Shibuya A. Gyoung YS. Yamamoto Y. J. Am. Chem. Soc.  1998,  120:  10262 
    Google Scholar
  • 3 Salter MM. Gevorgyan V. Saito S. Yamamoto Y. J. Chem. Soc., Chem. Commun.  1996,  17 
    Google Scholar
  • 4 Nakamura I. Bajracharya GB. Yamamoto Y. J. Org. Chem.  2003,  68:  2297 
    CrossrefGoogle Scholar
  • 5 Oh BH. Nakamura I. Yamamoto Y. Tetrahedron Lett.  2002,  43:  9625 
    CrossrefGoogle Scholar
  • 6a Tsukada N. Shibuya A. Nakamura I. Yamamoto Y. J. Am. Chem. Soc.  1997,  119:  8123 
    CrossrefGoogle Scholar
  • 6b Tsukada N. Shibuya A. Nakamura I. Kitahara H. Yamamoto Y. Tetrahedron  1999,  55:  8833 
    CrossrefGoogle Scholar
  • 7a Yamamoto Y. Al-Masum M. Asao N. J. Am. Chem. Soc.  1994,  116:  6019 
    CrossrefGoogle Scholar
  • 7b For hydroamination of allenes, see: Yamamoto Y. Al-Masum M. Fujiwara N. J. Chem. Soc., Chem. Commun.  1996,  381 
    CrossrefGoogle Scholar
  • 7c Yamamoto Y. Al-Masum M. Takeda A. J. Chem. Soc., Chem. Commun.  1996,  831 
    CrossrefGoogle Scholar
  • 7d Yamamoto Y. Al-Masum M. Fujiwara N. Asao N. Tetrahedron Lett.  1995,  36:  2811 
    CrossrefGoogle Scholar
  • 7e Yamamoto Y. Al-Masum M. Synlett  1995,  969 
    CrossrefGoogle Scholar
  • 7f Meguro M. Kamijo S. Yamamoto Y. Tetrahedron Lett.  1996,  37:  7453 
    CrossrefGoogle Scholar
  • 7g The addition of the C-H bond of carbon pronucleophiles to allenes was also reported by other groups, see: Besson L. Jacques G. Cazes B. Tetrahedron Lett.  1995,  36:  3853 
    CrossrefGoogle Scholar
  • 7h Trost BM. Gerusz VJ. J. Am. Chem. Soc.  1995,  117:  5156 
    CrossrefGoogle Scholar
  • 7i Trost BM. Jakel C. Plietker B. J. Am. Chem. Soc.  2003,  125:  4438 
    CrossrefGoogle Scholar
  • 7j For a recent review, see: Zimmer R., Dinesh C. U., Nandanan E., Khan F. A.; Chem. Rev.; 2000, 100: 3067
    Crossref
  • 8a A highly regio- and stereoselective intermolecular addition of amines to allenes using Pd(0)/CH3COOH is known, see: Al-Masum M. Meguro M. Yamamoto Y. Tetrahedron Lett.  1997,  38:  6071 
    CrossrefGoogle Scholar
  • 8b The reactions including the formation of π-allylpalladium intermediates are facilitated in the presence of an acid, see: Manabe K. Kobayashi S. Org. Lett.  2003,  5:  3241 
    CrossrefGoogle Scholar
  • 8c Kadota I. Shibuya A. Lutete ML. Yamamoto Y. J. Org. Chem.  1999,  64:  4570 
    CrossrefGoogle Scholar
  • 8d Lutete ML. Kadota I. Shibuya A. Yamamoto Y. Heterocycles  2002,  58:  347 
    CrossrefGoogle Scholar
  • 8e Kadota I. Lutete ML. Shibuya A. Yamamoto Y. Tetrahedron Lett.  2001,  42:  6207 
    CrossrefGoogle Scholar
  • 8f Zhang W. Haight AR. Hsu MC. Tetrahedron Lett.  2002,  43:  6575 
    CrossrefGoogle Scholar
  • 8g For a recent report on Pd(0)/acetic acid catalyzed regio- and stereoselective addition of organoboronic acids to allenes, see: Ma S. Jiao N. Ye L. Chem.-Eur. J.  2003,  9:  6049 
    CrossrefGoogle Scholar
  • 9 Al-Masum M. Yamamoto Y. J. Am. Chem. Soc.  1998,  120:  3809 
    Google Scholar
  • 10 Ranu BC. Samanta S. J. Org. Chem.  2003,  68:  7130 
    CrossrefGoogle Scholar
  • 11 Manabe K. Kobayashi S. Org. Lett.  2003,  5:  3241 
    CrossrefPubMedGoogle Scholar
  • 12 Rene Q. Bernard K. Francois L. Mohammed A. Synth. Commun.  1998,  18:  1213 
    Google Scholar
  • 13 Varghese JP. Zouev I. Aufauvre L. Knochel P. Marek I. Eur. J. Org. Chem.  2002,  4151 
    CrossrefGoogle Scholar
  • 14 Tanabe M. Yamazawa H. Osakada K. Organometallics  2001,  20:  4451 
    CrossrefGoogle Scholar
  • 15 Huang CW. Shanmugasundaram M. Chang H.-M. Cheng C.-H. Tetrahedron  2003,  59:  3635 
    CrossrefGoogle Scholar