An unusual Me3SiI-promoted [4+2] annulation and reduction: an efficient approach to construct 4H-benzopyrans

Feijun Wang; Mingliang Qu; Feng Chen; Li Li; Min Shi

doi:10.1039/C1CC16028A

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An unusual Me₃SiI-promoted [4+2] annulation and reduction: an efficient approach to construct 4H-benzopyrans†

Feijun Wang,*^a Mingliang Qu,^a Feng Chen,*^a Li Li^a and Min Shi*^ab

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* Corresponding authors

^a Key Laboratory for Advanced Materials and Institute of Fine Chemicals, East China University of Science and Technology, 130 MeiLong Road, Shanghai 200237, P. R. China
E-mail: feijunwang@ecust.edu.cn, fengchen@ecust.edu.cn

^b State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Road, Shanghai 200032, P. R. China
E-mail: mshi@mail.sioc.ac.cn

Abstract

Me₃SiI-promoted reaction of salicylic aldehydes with β-dicarbonyl compounds provided a facile way to construct 4H-benzopyrans in moderate to good yields. This tandem reaction proceeds with high efficiency through nucleophilic addition, silyl enol ether formation, substitution, reduction, and intramolecular nucleophilic cyclization.

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Article information

DOI: https://doi.org/10.1039/C1CC16028A
Article type: Communication
Submitted: 28 Sep 2011
Accepted: 26 Oct 2011
First published: 15 Nov 2011

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Chem. Commun., 2012,48, 437-439

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An unusual Me₃SiI-promoted [4+2] annulation and reduction: an efficient approach to construct 4H-benzopyrans

F. Wang, M. Qu, F. Chen, L. Li and M. Shi, Chem. Commun., 2012, 48, 437 DOI: 10.1039/C1CC16028A

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