Citation: Naichen Zhang, Yuanzhi Ye, Lu Bai, Jingjing Liu, Han Wang, Xinjun Luan. Transition metal-free dearomatization of halonaphthols with C(sp³)-electrophiles[J]. Chinese Chemical Letters, ;2022, 33(5): 2411-2414. doi: 10.1016/j.cclet.2021.10.037 shu

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

Key Laboratory of Synthetic and Natural Functional Molecule of the Ministry of Education, College of Chemistry & Materials Science, Northwest University, Xi'an 710127, China

hanwang@nwu.edu.cn

xluan@nwu.edu.cn

Received Date: 10 September 2021
Revised Date: 11 October 2021
Accepted Date: 15 October 2021
Available Online: 22 October 2021

Figures(7)

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 S_N2 reaction pathway.
- Halonaphthol,
- Fluoronaphol,
- Benzylation,
- Allylation,
- Cyclic enone
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Transition metal-free dearomatization of halonaphthols with C(sp3)-electrophiles

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通讯作者: 陈斌, bchen63@163.com

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