| Intramolecular Biaryl Oxidative Coupling of Stilbene Substrates by Vanadium Oxytrichloride (VOCl3): Facile Synthesis of Substituted Phenanthrene Derivatives |
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| 作者姓名： | JIN Zhong
WANG Qing-Min
HUANG Run-Qiu
LIU Yu-Xiu
LI Hao
LI Shi-Pu |
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| 作者单位： | JIN,Zhong（Institute and State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin 300071）
WANG,Qing-Min（Institute and State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin 300071）
HUANG,Run-Qiu（Institute and State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin 300071）
LIU,Yu-Xiu（Institute and State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin 300071）
LI,Hao（Institute and State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin 300071）
LI,Shi-Pu（Institute and State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin 300071） |
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| 基金项目： | 国家重点基础研究发展计划(973计划)，国家自然科学基金，Foundation of Author of National Excellent Doctoral Dissertation of China |
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| 摘 要： | The biaryl unit is extensively presented in many classes of natural products, such as polyketides, terpenes, lignanes,coumarins, flavonoids, tannins, and many alkaloids.1] It has long been recognized that an intramolecular oxidative phenolic or nonphenolic coupling reaction serves as the key step in the biosynthesis of these natural products, and the non-enzymic analogue of this transformation can lead the elegantly simple syntheses of these compounds.2] During the last decade, a large number of oxidative coupling reagents, such as ferric chloride (FeCl3), phenyliodine(Ⅲ)bis(trifluoroacetate) (PIFA), lead(Ⅳ) tetraacetate Pb(OAc)4], thallium(Ⅲ) triflouroacetate (TTFA), as well as vanadium oxytrifluoride (VOF3),3,4] have been developed for this target. However, extensive application of this synthetic potential has been limited by low yields and unexpected side reactions usually encountered.
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Intramolecular Biaryl Oxidative Coupling of Stilbene Substrates by Vanadium Oxytrichloride (VOCl3):Facile Synthesis of Substituted Phenanthrene Derivatives |
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| JIN,Zhong,WANG,Qing-Min,HUANG,Run-Qiu,LIU,Yu-Xiu,LI Hao,LI,Shi-Pu.Intramolecular Biaryl Oxidative Coupling of Stilbene Substrates by Vanadium Oxytrichloride (VOCl3): Facile Synthesis of Substituted Phenanthrene Derivatives[J].Chinese Journal of Organic Chemistry,2004,24(Z1):199. |
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| Authors: | JIN Zhong WANG Qing-Min HUANG Run-Qiu LIU Yu-Xiu LI Hao LI Shi-Pu |
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| Abstract: | The biaryl unit is extensively presented in many classes of natural products, such as polyketides, terpenes, lignanes,coumarins, flavonoids, tannins, and many alkaloids.1] It has long been recognized that an intramolecular oxidative phenolic or nonphenolic coupling reaction serves as the key step in the biosynthesis of these natural products, and the non-enzymic analogue of this transformation can lead the elegantly simple syntheses of these compounds.2] During the last decade, a large number of oxidative coupling reagents, such as ferric chloride (FeCl3), phenyliodine(Ⅲ)bis(trifluoroacetate) (PIFA), lead(Ⅳ) tetraacetate Pb(OAc)4], thallium(Ⅲ) triflouroacetate (TTFA), as well as vanadium oxytrifluoride (VOF3),3,4] have been developed for this target. However, extensive application of this synthetic potential has been limited by low yields and unexpected side reactions usually encountered. |
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