Coupling Reaction of Azulenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolanes with Haloazulenes

Kei Kurotobi; Hiroshi Tabata; Masato Miyauchi; Toshihiro Murafuji; Yoshikazu Sugihara

doi:10.1055/s-2002-31947

PAPER

Coupling Reaction of Azulenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolanes with Haloazulenes

Kei Kurotobi, Hiroshi Tabata, Masato Miyauchi, Toshihiro Murafuji*, Yoshikazu Sugihara*
Department of Chemistry, Faculty of Science, Yamaguchi University, Yamaguchi City 753-8512, Japan
Fax: +81839335768; e-Mail: murafuji@po.cc.yamaguchi-u.ac.jp; sugihara@po.cc.yamaguchi-u.ac.jp;

Abstract

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Abstract

In order to study the physicochemical properties of azulene oligomers, the synthesis and a coupling reaction of 2-(2-amino-1,3-bisethoxycarbonyl-6-azulenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1) and 2-(2-azulenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (2) were examined.

Key words

arenes - azulene - boron - borylazulene - cross-coupling

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References

<A NAME="RF00902SS-1">1</A> Gerson F. Lopez J. Metzger A. Helv. Chim. Acta 1980, 63: 2135

<A NAME="RF00902SS-2">2</A> Morita T. Takase K. Bull. Chem. Soc. Jpn. 1982, 55: 1144

<A NAME="RF00902SS-3A">3a</A> Hanke M. Jutz C. Angew. Chem. Int. Ed. Engl. 1979, 18: 214

<A NAME="RF00902SS-3B">3b</A> Hanke M. Jutz C. Synthesis 1980, 31

<A NAME="RF00902SS-4A">4a</A> Iyoda M. Sato K. Oda M. Tetrahedron Lett. 1985, 26: 3828

<A NAME="RF00902SS-4B">4b</A> For the coupling reaction of azulenes, see: Okujima T. Ito N. Morita N. Tetrahedron Lett. 2002, 43: 1261

<A NAME="RF00902SS-4C">4c</A> See also: Dyker G. Borowski S. Heierrmann J. Körning J. Opwis K. Henkel G. Köckerling M. J. Organomet. Chem. 2000, 606: 108

<A NAME="RF00902SS-4D">4d</A> See also: Balschukat D. Dehmlow CV. Chem. Ber. 1986, 119: 2272

<A NAME="RF00902SS-5">5</A> Miyaura N. Suzuki A. Chem. Rev. 1995, 95: 2457

<A NAME="RF00902SS-6">6</A> For generation of 2-azulenyllithium from 2-iodoazulene, see: Shimoyama H. Ito A. Takeda K. Hamazaki H. Ota A. Fujimori K. In The Abstracts of the 29th Symposium on Structural Organic Chemistry Saitama: Japan, September 20-22; 1999. p.310

<A NAME="RF00902SS-7A">7a</A> Ishiyama T. Murata M. Miyaura N. J. Org. Chem. 1995, 60: 7508

<A NAME="RF00902SS-7B">7b</A> For a recent paper for palladium-catalyzed borylation with aryl halides, see: Murata M. Oyama T. Watanabe S. Masuda Y. J. Org. Chem. 2000, 65: 164

<A NAME="RF00902SS-8">8</A> Hyslop AG. Kellett MA. Iovine PM. Therien MJ. J. Am. Chem. Soc. 1998, 120: 12676

<A NAME="RF00902SS-9">9</A> Nozoe T. Seto S. Matsumura S. Bull. Chem. Soc. Jpn. 1962, 35: 1990