Single-Electron Oxidation/Alterable C3- and C10-Arylation of 9-MeO-phenanthrene.

Wang, Tao; Ma, Huijun; Zhang, Shitong; Li, Zong-Jun; Zhang, Minghao; Li, Feng; Sun, Fuxing; Xiang, Jinbao; Ke, Mufang; Wang, Qifeng

Wang, Tao; Ma, Huijun; Zhang, Shitong; Li, Zong-Jun; Zhang, Minghao; Li, Feng; Sun, Fuxing; Xiang, Jinbao; Ke, Mufang; Wang, Qifeng.

Afiliação

Wang T; International Joint Research Laboratory of Nano-Micro Architecture Chemistry (NMAC), Department of Organic Chemistry, College of Chemistry , Jilin University , 2699 Qianjin Street , Changchun 130012 , P. R. China.
Ma H; International Joint Research Laboratory of Nano-Micro Architecture Chemistry (NMAC), Department of Organic Chemistry, College of Chemistry , Jilin University , 2699 Qianjin Street , Changchun 130012 , P. R. China.
Zhang S; International Joint Research Laboratory of Nano-Micro Architecture Chemistry (NMAC), Department of Organic Chemistry, College of Chemistry , Jilin University , 2699 Qianjin Street , Changchun 130012 , P. R. China.
Li ZJ; State Key Laboratory of Electroanalytical Chemistry, Changchun Institute of Applied Chemistry , Chinese Academy of Sciences , Changchun , Jilin 130022 , P. R. China.
Zhang M; International Joint Research Laboratory of Nano-Micro Architecture Chemistry (NMAC), Department of Organic Chemistry, College of Chemistry , Jilin University , 2699 Qianjin Street , Changchun 130012 , P. R. China.
Li F; International Joint Research Laboratory of Nano-Micro Architecture Chemistry (NMAC), Department of Organic Chemistry, College of Chemistry , Jilin University , 2699 Qianjin Street , Changchun 130012 , P. R. China.
Sun F; International Joint Research Laboratory of Nano-Micro Architecture Chemistry (NMAC), Department of Organic Chemistry, College of Chemistry , Jilin University , 2699 Qianjin Street , Changchun 130012 , P. R. China.
Xiang J; International Joint Research Laboratory of Nano-Micro Architecture Chemistry (NMAC), Department of Organic Chemistry, College of Chemistry , Jilin University , 2699 Qianjin Street , Changchun 130012 , P. R. China.
Ke M; International Joint Research Laboratory of Nano-Micro Architecture Chemistry (NMAC), Department of Organic Chemistry, College of Chemistry , Jilin University , 2699 Qianjin Street , Changchun 130012 , P. R. China.
Wang Q; International Joint Research Laboratory of Nano-Micro Architecture Chemistry (NMAC), Department of Organic Chemistry, College of Chemistry , Jilin University , 2699 Qianjin Street , Changchun 130012 , P. R. China.

Org Lett ; 20(12): 3591-3595, 2018 06 15.

Article em En | MEDLINE | ID: mdl-29851491

ABSTRACT

ABSTRACT

A reactivity pattern for C3-arylation of 9-MeO-phenanthrene has been established for the first time by using 2-naphthyl amines as coupling partners. A series of phenanthrene- and naphthalene-based multifunctionalized polycyclic aromatic hydrocarbons have been obtained in good to excellent yields. Alternative C10-arylation of 9-MeO-phenanthrene has also been accomplished, using 2-naphthalenol derivatives as coupling partners. Trifluoroacetic acid is found crucial for the regioselectivity. Density functional theory calculations and electrochemical analyses have been performed to rationalize the reaction mechanism.

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Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Idioma: En Revista: Org Lett Assunto da revista: BIOQUIMICA Ano de publicação: 2018 Tipo de documento: Article

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