CuO/I2-mediated intramolecular annulation for the synthesis of 2-aroyl-3-hydroxy-4-iodonaphthalenes

Qun Cai; Yan Yang; Deng-Kui Li; Feng-Cheng Jia; Cheng Xu; An-Xin Wu

doi:10.1039/C5RA17651D

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CuO/I₂-mediated intramolecular annulation for the synthesis of 2-aroyl-3-hydroxy-4-iodonaphthalenes†

Qun Cai,^a Yan Yang,^a Deng-Kui Li,^a Feng-Cheng Jia,^a Cheng Xu^a and An-Xin Wu*^a

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* Corresponding authors

^a Key Laboratory of Pesticide & Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, Wuhan 430079, P. R. China
E-mail: chwuax@mail.ccnu.edu.cn

Abstract

A novel strategy has been developed for the direct synthesis of 2-aroyl-3-hydroxy-4-iodonaphthalenes from easily available (Z)-2-(hetero)arylidene-1-(hetero)arylbutane-1,3-diones in the presence of copper(II) oxide and iodine. This domino process involves consecutive methyl iodination/carbon–carbon double bond isomerization/6π-electrocyclization/aromatization/arene iodination sequences.

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Article information

DOI: https://doi.org/10.1039/C5RA17651D
Article type: Communication
Submitted: 31 Aug 2015
Accepted: 12 Oct 2015
First published: 13 Oct 2015

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RSC Adv., 2015,5, 89427-89430

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CuO/I₂-mediated intramolecular annulation for the synthesis of 2-aroyl-3-hydroxy-4-iodonaphthalenes

Q. Cai, Y. Yang, D. Li, F. Jia, C. Xu and A. Wu, RSC Adv., 2015, 5, 89427 DOI: 10.1039/C5RA17651D

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