| DDQ/TFA： an Efficient Nonmetallic Reagent System for the Oxidative Coupling to Construct Phenanthrene Rings |
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| 基金项目： | Supported by the National Key Project for Basic Research of China（No.2010CB126100）, the National Natural Science Foundation of China（Nos.21132003, 21121002, 21372131） and the Specialized Research Fund for the Doctoral Program of Higher Education of China（No.20120031110010）. |
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| 摘 要： | A mild synthetic method of a series of phenanthrenes with different substituents on the phenanthrene ring is described.The method involves intramolecular oxidative coupling with 2,3-dichloro-5,6-dicyanobenzoquinone （DDQ）/trifluoroacetic acid（TFA） as oxidant to produce phenanthrenes in high yields and is fit for large-scale preparation.Furthermore,DDQ can be regenerated by a simple oxidation.The present approach solves a key step for the synthesis of polycyclic structures related to an alkaloid tylophorine.
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| 关 键 词： | 氧化偶联 DDQ TFA 非金属 菲 戒指 系统 试剂 |
DDQ/TFA: an Efficient Nonmetallic Reagent System for the Oxidative Coupling to Construct Phenanthrene Rings |
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| LI Ling HU Yanna WANG Kailiang WANG Qingmin. DDQ/TFA: an Efficient Nonmetallic Reagent System for the Oxidative Coupling to Construct Phenanthrene Rings[J]. Chemical Research in Chinese University, 2014, 30(4): 619-623. DOI: 10.1007/s40242-014-3561-9 |
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| Authors: | LI Ling HU Yanna WANG Kailiang WANG Qingmin |
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| Affiliation: | State Key Laboratory of Elemento-Organic Chemistry and Research Institute of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, P. R. China |
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| Abstract: | A mild synthetic method of a series of phenanthrenes with different substituents on the phenanthrene ring is described. The method involves intramolecular oxidative coupling with 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ)/trifluoroacetic acid(TFA) as oxidant to produce phenanthrenes in high yields and is fit for large-scale preparation. Furthermore, DDQ can be regenerated by a simple oxidation. The present approach solves a key step for the synthesis of polycyclic structures related to an alkaloid tylophorine. |
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| Keywords: | Intramolecular oxidative coupling 2,3-Dichloro-5,6-dicyanobenzoquinone（DDQ） 1,2-Diarylethylene Phenanthrene ring Alkaloid |
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