Synthesis of -arylphenol derivatives acid-promoted rearrangement of cyclohexadienones

A highly effective strategy for the synthesis of meta -arylphenol derivatives through the selective rearrangement of 4-alkyl-4-aryl-2,5-cyclohexadienones under metal-free conditions was developed, in which acid-promoted [1,2]-migration of the aryl group at C-4 occurred exclusively when the alkyl gro...

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Published inOrganic & biomolecular chemistry Vol. 21; no. 42; pp. 8573 - 8578
Main Authors Xie, Hongyan, Zhang, Minxiang, Fang, Xueyu, Yan, Zhaohua, Yao, Hua
Format Journal Article
Published 01.11.2023
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Summary:A highly effective strategy for the synthesis of meta -arylphenol derivatives through the selective rearrangement of 4-alkyl-4-aryl-2,5-cyclohexadienones under metal-free conditions was developed, in which acid-promoted [1,2]-migration of the aryl group at C-4 occurred exclusively when the alkyl group at C-4 was a methyl group. Treatment of 4-methyl-4-aryl-2,5-cyclohexadienones with 37% HCl in Ac 2 O at room temperature provided polysubstituted meta -arylphenyl acetates in 75-94% yields. The application of this protocol in the synthesis of polycyclic aromatic compounds was also described. A highly selective acid-promoted aryl [1,2]-rearrangement of 4-methyl-4-aryl-2,5-cyclohexadienones with 37% HCl in Ac 2 O was developed, and the corresponding polysubstituted meta -arylphenyl acetates were smoothly generated in 75-94% yields.
Bibliography:https://doi.org/10.1039/d3ob01363d
Electronic supplementary information (ESI) available. See DOI
ISSN:1477-0520
1477-0539
DOI:10.1039/d3ob01363d