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Direct synthesis of phenanthrenyl triflates from 1-biphenylyl-2-diazo-2-aryl ketones and triflic anhydride.
Liu, Yueqiang; Zhang, Sheng; Feng, Xiujuan; Yu, Xiaoqiang; Yamamoto, Yoshinori; Bao, Ming.
  • Liu Y; State Key Laboratory of Fine Chemicals, Frontier Science Center for Smart Materials, School of Chemical Engineering, Dalian University of Technology, Dalian 116024, China. shengzhang@dlut.edu.cn.
  • Zhang S; State Key Laboratory of Fine Chemicals, Frontier Science Center for Smart Materials, School of Chemical Engineering, Dalian University of Technology, Dalian 116024, China. shengzhang@dlut.edu.cn.
  • Feng X; State Key Laboratory of Fine Chemicals, Frontier Science Center for Smart Materials, School of Chemical Engineering, Dalian University of Technology, Dalian 116024, China. shengzhang@dlut.edu.cn.
  • Yu X; State Key Laboratory of Fine Chemicals, Frontier Science Center for Smart Materials, School of Chemical Engineering, Dalian University of Technology, Dalian 116024, China. shengzhang@dlut.edu.cn.
  • Yamamoto Y; State Key Laboratory of Fine Chemicals, Frontier Science Center for Smart Materials, School of Chemical Engineering, Dalian University of Technology, Dalian 116024, China. shengzhang@dlut.edu.cn.
  • Bao M; Department of Chemistry, Graduate School of Science, Tohoku University, Sendai 980-8578, Japan.
Org Biomol Chem ; 22(6): 1141-1145, 2024 Feb 07.
Article en En | MEDLINE | ID: mdl-38214226
ABSTRACT
A strategy for direct synthesis of phenanthrenyl triflates from 1-biphenylyl-2-diazo-2-aryl ketones and triflic anhydride is described. The reaction of 1-biphenylyl-2-diazo-2-aryl ketones with triflic anhydride proceeded smoothly in the presence of 2,6-di-tert-butylpyridine under mild conditions to produce phenanthrenyl triflates in high to excellent yields. The phenanthrenyl triflate products were demonstrated to be utilized as coupling partners in various coupling reactions. The proposed mechanism involves an intramolecular Friedel-Crafts reaction of a vinyl cation intermediate formed in situ.
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Texto completo: 1 Banco de datos: MEDLINE Idioma: En Año: 2024 Tipo del documento: Article
Texto completo
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Texto completo: 1 Banco de datos: MEDLINE Idioma: En Año: 2024 Tipo del documento: Article