Synthesis 2006(21): 3611-3616  
DOI: 10.1055/s-2006-950220
PAPER
© Georg Thieme Verlag Stuttgart · New York

Palladium-Catalyzed, Triethylborane-Promoted C-Allylation of Naphthols and Benzene Polyols by Direct Use of Allyl Alcohols

Masanari Kimuraa, Miki Fukasakaa, Yoshinao Tamaru*b
a Graduate School of Science and Technology, Nagasaki University, 1-14 Bunkyo, Nagasaki 852-8521, Japan
b Department of Applied Chemistry, Faculty of Engineering, Nagasaki University, 1-14 Bunkyo, Nagasaki 852-8521, Japan
Fax: +81(95)8192677; e-Mail: tamaru@net.nagasaki-u.ac.jp;
Further Information

Publication History

Received 30 May 2006
Publication Date:
04 September 2006 (online)

Abstract

The combination of a catalytic amount of Pd(0) species and triethylborane promotes the C-allylation of benzene polyols and naphthols at room temperature to 50 °C by the direct use of a variety of allylic alcohols; Exhaustive allylation of 1,3-benzenediol and 1,3,5-benzenetriol provides penta-allylation and hexa-allylation products, respectively, in good yields.

    References

  • 1a Yasuda M. Somyo T. Baba A. Angew. Chem. Int. Ed.  2006,  45:  793 
  • 1b Li D.-P. Guo Y.-C. Ding Y. Xiao W.-J. Chem. Commun.  2006,  799 
  • 1c Mertins K. Iovel I. Kischek J. Zapf A. Beller M. Angew. Chem. Int. Ed.  2005,  44:  238 
  • 1d Iovel I. Mertins K. Kischek J. Zapf A. Beller M. Angew. Chem. Int. Ed.  2005,  44:  3913 
  • 1e Evans DA. Fandrich KR. Song H.-J. J. Am. Chem. Soc.  2005,  127:  8942 
  • 1f Palomo C. Oiarbide M. Kardak BG. Garcia JM. Linden A. J. Am. Chem. Soc.  2005,  127:  4154 
  • 1g For a comprehensive review on Friedel-Crafts alkylations, see: Olah GA. Krishnamurti R. Prakash GKS. In Comprehensive Organic Synthesis   Vol. 3:  Trost BM. Pergamon; Oxford: 1991.  Chap. 1.8.
  • 2a Patrick VRS. Gareth DJ. J. Chem. Soc., Perkin Trans. 1  1977,  2585 
  • 2b Edward C. Gareth DJ. Patrick VRS. J. Chem. Soc., Perkin Trans. 1  1975,  96 
  • 3 Taura F. Morimoto S. Shoyama Y. J. Biol. Chem.  1996,  271:  17411 
  • 4 Liu K. Xu L. Berger JP. MacNaul KL. Zhou G. Doebber TW. Forrest MJ. Moller DE. Jones AB. J. Med. Chem.  2005,  48:  2262 
  • 5a Min J.-H. Lee J.-S. Yang J.-D. Koo S. J. Org. Chem.  2003,  68:  7925 
  • 5b Negishi E. Liou S.-Y. Xu C. Huo S. Org. Lett.  2002,  4:  261 
  • 5c Lipshutz BH. Kim S. Mollard P. Stevens KL. Tetrahedron  1998,  54:  1241 
  • 6a Gozzo FC. Fernandes SA. Rodrigues DC. Eberlin MN. Marsaioli AJ. J. Org. Chem.  2003,  68:  5493 
  • 6b Sharma GVM. Ilangovan A. Sreenivas P. Mahalingam AK. Synlett  2000,  615 
  • 6c Anjaneyulu ASR. Isaa BM. J. Chem. Soc., Perkin Trans. 1  1990,  993 
  • 6d Harwood LM. Oxford AJ. Thomson C. J. Chem. Soc., Perkin Trans. 1  1987,  1615 
  • 6e Hurd CD. Greemgard H. Pilgrim FD. J. Am. Chem. Soc.  1930,  52:  1700 
  • 7a Kimura M. Futamata M. Mukai R. Tamaru Y. J. Am. Chem. Soc.  2005,  127:  4592 
  • 7b Trost BM. Quancard J. J. Am. Chem. Soc.  2006,  128:  6314 
  • 8 Kimura M. Fukasaka M. Tamaru Y. Heterocycles  2006,  67:  535 
  • 9 Kimura M. Ezoe A. Mori M. Iwata K. Tamaru Y. J. Am. Chem. Soc.  2006,  128:  8559 
  • 10 Tada Y. Satake A. Shimizu I. Yamamoto A. Chem. Lett.  1996,  1021 
  • 11 O-Allylation of phenol with allyl alcohol promoted by Pd-catalyst and Ti(Oi-Pr)4: Satoh T. Ikeda M. Miura M. Nomura M. J. Org. Chem.  1997,  62:  4877 
  • 12 Stein AR. Can. J. Chem.  1965,  43:  1508 
  • Pd·BEt3-promoted direct allylations of a variety of nucleophiles with allylic alcohols have been developed in our laboratories:
  • 13a Tamaru Y. Eur. J. Org. Chem.  2005,  2647 
  • 13b Kimura M. Futamata M. Shibata K. Tamaru Y. Chem. Commun.  2003,  234 
  • 13c Kimura M. Mukai R. Tanigawa N. Tanaka S. Tamaru Y. Tetrahedron  2003,  59:  7767 
  • 13d Kimura M. Horino Y. Mukai R. Tanaka S. Tamaru Y. J. Am. Chem. Soc.  2001,  123:  10401 
  • 13e Horino Y. Naito M. Kimura M. Tanaka S. Tamaru Y. Tetrahedron Lett.  2001,  42:  3113 
  • 13f Tamaru Y. Horino Y. Araki M. Tanaka S. Kimura M. Tetrahedron Lett.  2000,  41:  5705 
  • 14a Li H. Homan AH. Lampkins AJ. Ghiviriga I. Castellano RK. Org. Lett.  2005,  7:  443 
  • 14b Bencze K. Z. Anal. Chem.  1962,  189:  309 
  • 15 Herzig J. Erthal B. Monatsh. Chem.  1910,  31:  827