Transition metal-free dearomatization of halonaphthols with C(sp3)-electrophiles

The first intermolecular electrophilic dearomatization of halonaphthols with benzyl/allyl bromides is described. Halonaphthols are used as carbon-nucleophiles in dearomatization to form three-dimensional cyclic enones with excellent chemoselectivity, in which etherification of phenolic hydroxyl grou...

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Bibliographic Details
Published in:Chinese chemical letters 2022-05, Vol.33 (5), p.2411-2414
Main Authors: Zhang, Naichen, Ye, Yuanzhi, Bai, Lu, Liu, Jingjing, Wang, Han, Luan, Xinjun
Format: Article
Language:English
Subjects:
Allylation
Benzylation
Cyclic enone
Fluoronaphol
Halonaphthol
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Summary:The first intermolecular electrophilic dearomatization of halonaphthols with benzyl/allyl bromides is described. Halonaphthols are used as carbon-nucleophiles in dearomatization to form three-dimensional cyclic enones with excellent chemoselectivity, in which etherification of phenolic hydroxyl group could be restrained well by using cesium carbonate as the base. A wide range of cyclic enones is directly prepared from various substituted benzyl/allyl bromides and halonaphthols. Mechanistic investigations suggest a direct SN2 reaction pathway. [Display omitted]
ISSN:1001-8417
1878-5964
DOI:10.1016/j.cclet.2021.10.037