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学科主题: 有机氟化学
题名: Rational synthesis of meso- or beta- fluoroalkylporphyrin derivatives via halo-fluoroalkylporphyrin precursors: Electronic and steric effects on regioselective electrophilic substitution in 5-fluoroalkyl-10,20-diarylporphyrins
其他题名: 通过卤代氟烷基化卟啉前体合理的合成meso-和β-氟烷基化卟啉:电子和为阻效益对5-氟烷基-10,20-二芳基卟啉亲电取代区域选择性的影响
作者: Jin LM(金利美) ; Chen L(陈亮) ; Yin JJ(尹娟娟) ; Zhou JM(周金明) ; Xiao JC(肖吉昌) ; Guo CC(郭灿城) ; Chen QY(陈庆云)
通讯作者: 郭灿城 ; 陈庆云
刊名: J. Org. Chem.
发表日期: 2006
卷: 71, 期:2, 页:527-536
收录类别: SCI
部门归属: 湖南大学化学化工学院; 中科院上海有机所有机氟化学重点实验室; 中科院上海应用物理研究所纳米生物医药室
英文摘要: Electrophilic nitration, formylation or bromination of metalated 5-fluoroalkyl-10,20-diphenylporphyrin (fluoroalkyl = CF3, ClCF2ClCF2, n-C6F13) proceeded with high regioselectivity, exclusively affording corresponding meso-substituted porphyrins, while the iodination reaction mainly took place at the adjacent site giving 2-iodo-10-fluoroalkyl-5,15-diphenylporphyrin. Suzuki, Sonogashira, and trifluoromethylation reactions of the obtained 5-bromo-15-fluoroalkyl-10,20-diphenylporphyrins or 2-iodo-10-fluoroalky-15,15-diphenylporphyrins could perform smoothly to give the corresponding various meso- or beta-functionalized fluoroalkylated porphyrin derivatives. Accordingly, two meso-to-meso butadiyne-bridged bisporphyrin dimers and two beta-to-beta butadiyne-linked dimeric porphyrins were prepared by the coupling reactions of 5-ethynyl-15-fluoroalkyl-10,20-diphenylporphyrins and 2-ethynyl-lo-fluoroalkyl-5,15-diphenylporphyrins, respectively.
语种: 英语
相关网址: 查看原文
WOS记录号: WOS:000234837500010
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内容类型: 期刊论文
URI标识: http://ir.sioc.ac.cn/handle/331003/13636
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,Yin JJ,et al. Rational synthesis of meso- or beta- fluoroalkylporphyrin derivatives via halo-fluoroalkylporphyrin precursors: Electronic and steric effects on regioselective electrophilic substitution in 5-fluoroalkyl-10,20-diarylporphyrins[J]. J. Org. Chem.,2006,71(2):527-536.
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