First intramolecular aromatic substitution by gold(III) of a ligand other than pyridine derivatives. Synthesis and crystal structure of the novel five-membered cycloaurated complex of 1-ethyl-2-phenylimidazole

Yoshio Fuchita; Hidenori Ieda; Mikio Yasutake

doi:10.1039/A908048A

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First intramolecular aromatic substitution by gold(III) of a ligand other than pyridine derivatives. Synthesis and crystal structure of the novel five-membered cycloaurated complex of 1-ethyl-2-phenylimidazole

Yoshio Fuchita,*^a Hidenori Ieda^a and Mikio Yasutake^b

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* Corresponding authors

^a Division of Molecular Chemistry, Graduate School of Science, Kyushu University at Ropponmatsu, Chuo-ku, Fukuoka, Japan
E-mail: fuchita@rc.kyushu-u.ac.jp

^b Institute for Fundamental Research of Organic Chemistry, Kyushu University, Hakozaki, Higashi-ku, Fukuoka, Japan

Abstract

Reactions of gold(III) compounds, AuCl₃·4H₂O and HAuCl₄·4H₂O, with 2-phenyl-1H-imidazole (Hpi) and 1-ethyl-2-phenylimidazole (Hepi) have been performed under various reaction conditions: Hpi afforded only the salt [H(Hpi)][AuCl₄], while Hepi produced both the salt [H(Hepi)][AuCl₄] and the adduct [AuCl₃(Hepi)]. Cycloauration of Hepi, the first example of cycloauration of a substrate other than pyridine derivatives, has been established by the formation of [AuCl₂(epi-C¹,N)] [epi = 2-(1-ethyl-2-imidazolyl)phenyl] from the reaction between the adduct [AuCl₃(Hepi)] and AgBF₄. The cyclometallated structure of Hepi has been confirmed by the X-ray crystallographic study of a derivative [AuCl(epi-C¹,N)(PPh₃)]PF₆.

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DOI: https://doi.org/10.1039/A908048A
Article type: Paper
Submitted: 06 Oct 1999
Accepted: 03 Dec 1999
First published: 27 Jan 2000

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J. Chem. Soc., Dalton Trans., 2000, 271-274

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First intramolecular aromatic substitution by gold(III) of a ligand other than pyridine derivatives. Synthesis and crystal structure of the novel five-membered cycloaurated complex of 1-ethyl-2-phenylimidazole

Y. Fuchita, H. Ieda and M. Yasutake, J. Chem. Soc., Dalton Trans., 2000, 271 DOI: 10.1039/A908048A

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Journal of the Chemical Society, Dalton Transactions

First intramolecular aromatic substitution by gold(III) of a ligand other than pyridine derivatives. Synthesis and crystal structure of the novel five-membered cycloaurated complex of 1-ethyl-2-phenylimidazole

Abstract

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First intramolecular aromatic substitution by gold(III) of a ligand other than pyridine derivatives. Synthesis and crystal structure of the novel five-membered cycloaurated complex of 1-ethyl-2-phenylimidazole

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