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PhI(OAc)2-mediated dialkoxylation of 4-aminostyrenes through a dearomatization process under metal-free conditions

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Abstract

A novel PhI(OAc)2-mediated dialkoxylation of 4-aminostyrenes has been developed. A range of 2,3-disubstituted 1,4-dioxane or 1,2-dimethoxyethane derivatives were formed in 15 to 95% yields with high diastereoselectivities. This transformation was distinct from the previously reported hypervalent iodine(III)-mediated dioxygenation reaction, a process via the formation of a cyclic iodonium ion intermediate. This protocol involves an oxidative dearomatization-induced nucleophilic attack and an aromatization-induced 1,6-conjugated addition.

Graphical abstract: PhI(OAc)2-mediated dialkoxylation of 4-aminostyrenes through a dearomatization process under metal-free conditions

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Publication details

The article was received on 03 Jul 2017, accepted on 27 Jul 2017 and first published on 28 Jul 2017


Article type: Research Article
DOI: 10.1039/C7QO00545H
Citation: Org. Chem. Front., 2017, Advance Article
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    PhI(OAc)2-mediated dialkoxylation of 4-aminostyrenes through a dearomatization process under metal-free conditions

    W. Wang, Q. He and R. Fan, Org. Chem. Front., 2017, Advance Article , DOI: 10.1039/C7QO00545H

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