DDQ/TFA: an Efficient Nonmetallic Reagent System for the Oxidative Coupling to Construct Phenanthrene Rings

doi:10.1007/s40242-014-3561-9

高等学校化学研究 ›› 2014, Vol. 30 ›› Issue (4): 619-623.doi: 10.1007/s40242-014-3561-9

DDQ/TFA: an Efficient Nonmetallic Reagent System for the Oxidative Coupling to Construct Phenanthrene Rings

LI Ling, HU Yanna, WANG Kailiang, WANG Qingmin

State Key Laboratory of Elemento-Organic Chemistry and Research Institute of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, P. R. China

出版日期:2014-08-01 发布日期:2014-02-25
通讯作者: WANG Qingmin E-mail:wangqm@nankai.edu.cn
基金资助:
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).

DDQ/TFA: an Efficient Nonmetallic Reagent System for the Oxidative Coupling to Construct Phenanthrene Rings

LI Ling, HU Yanna, WANG Kailiang, WANG Qingmin

State Key Laboratory of Elemento-Organic Chemistry and Research Institute of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, P. R. China

Online:2014-08-01 Published:2014-02-25
Contact: WANG Qingmin E-mail:wangqm@nankai.edu.cn
Supported by:
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).

摘要/Abstract

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.

关键词: Intramolecular oxidative coupling, 2,3-Dichloro-5,6-dicyanobenzoquinone(DDQ), 1,2-Diarylethylene, Phenanthrene ring, Alkaloid

Abstract:

Key words: Intramolecular oxidative coupling, 2,3-Dichloro-5,6-dicyanobenzoquinone(DDQ), 1,2-Diarylethylene, Phenanthrene ring, Alkaloid

LI Ling, HU Yanna, WANG Kailiang, WANG Qingmin. DDQ/TFA: an Efficient Nonmetallic Reagent System for the Oxidative Coupling to Construct Phenanthrene Rings[J]. 高等学校化学研究, 2014, 30(4): 619-623.

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 Universities, 2014, 30(4): 619-623.

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DDQ/TFA: an Efficient Nonmetallic Reagent System for the Oxidative Coupling to Construct Phenanthrene Rings

DDQ/TFA: an Efficient Nonmetallic Reagent System for the Oxidative Coupling to Construct Phenanthrene Rings

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