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...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_(N)2 reaction pathway.展开更多
基金The National Natural Science Foundation of China(Nos.21901203,22171225,21925108)the Education Department of Shaanxi Province(No.20JK0934)are acknowledged for financial support.
文摘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_(N)2 reaction pathway.
