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学科主题: 有机氟化学
题名: Copper-induced fluoroalkylation of porphyrins: solvent-dependent synthesis of fluoroalkyl chlorins and porphyrins from fluoroalkyl iodides methoxychlorin
其他题名: 铜引发的卟啉氟烷基化:依赖溶剂地从氟烷基碘合成氟烷基二氢卟吩和卟啉
作者: Jin LM(金利美) ; Chen L(陈亮) ; Guo CC(郭灿城) ; Chen QY(陈庆云)
通讯作者: 郭灿城 ; 陈庆云
刊名: J. Porphyr. Phthalocyanines
发表日期: 2005-01-01
卷: 9, 期:2, 页:109-120
收录类别: SCI
部门归属: 上海有机化学研究所元素有机化学研究室; 湖南大学
英文摘要: Treatment of copper(II) or nickel(II) porphyrins with fluoroalkyl iodides (RfI) in the presence of copper powder in dioxane, diglyme(DG) or tetrahydrofuran(THF) at 70-90 degrees C gave beta-fluoroalkyl chlorins in moderate yields. Unexpectedly, when dimethylsulphoxide (DMSO), hexamethylphosphoric triamide (HMPA) or N,N-dimethyiformamide (DMF) was used as the solvent, with chlorobenzene as aco-solvent, the beta-fluoroalkylporphyrins were obtained. In the first three solvents the reaction can be completely suppressed by p-dinitrobenzene (p-DNB) or hydroquione (HQ), but not at all in the last three solvents. Apparently, a single electron-transfer mechanism may be involved in the formation of beta-fluoroalkyl chlorins while fluoroalkylcopper intermediates may play a role in the production of beta-fluoroalkylporphyrins. The metallofluoroalkylchlorins can be converted quantitatively to 2-hydoxyl-3-fluoroalkylchlorins by air/SiO2 or air/Al2O1. Additionally, the metallofluoroalkylchlorins and metallofluoroalkylporphyrins can be converted into the corresponding free-base chlorins and porphyrins, respectively, with H2SO4. On the other hand, the metallohydoxyfluoroalkylchlorins under the same conditions afforded beta-fluoroalkylporphyrins. Metallohydroxyfluoroalkylchlorins were readily also etherified to the corresponding metallomethoxyfluoroalkylchlorins with dimethyl sulfate (Me2SO4). Copyright (c) 2005 Society of Porphyrins & Phthalocyanines.
语种: 英语
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内容类型: 期刊论文
URI标识: http://ir.sioc.ac.cn/handle/331003/13592
Appears in Collections:中科院有机氟化学重点实验室_期刊论文

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Recommended Citation:
Jin LM,Chen L,Guo CC,et al. Copper-induced fluoroalkylation of porphyrins: solvent-dependent synthesis of fluoroalkyl chlorins and porphyrins from fluoroalkyl iodides methoxychlorin[J]. J. Porphyr. Phthalocyanines,2005,9(2):109-120.
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