Multivalent Functionalization of Cyclodextrins by Photochemical Thiol-Ene Addition Reaction

Multivalent Functionalization of Cyclodextrins by Photochemical Thiol-Ene Addition Reaction
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光化学硫醇-烯加成反应对环糊精进行多价官能化

DOI:
10.1002/ejoc.201300880
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发表时间:
2013
影响因子:
2.8
通讯作者:
Becker
Becker
中科院分区:
化学3区
文献类型:
--
作者:
Becker

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环糊精是超分子化学中最常用的主体化合物之一。在本文中,我们描述了一种通过光化学硫醇-烯烃加成反应(“硫醇-烯点击化学”)实现环糊精多价官能化的通用方法。从在2-OH、3-OH和/或6-OH位置烯丙基化的环糊精开始,可以以良好至优异的产率引入一系列硫醇。通过使用被羟基、羧酸、酯、保护胺和四甘醇基团取代的烷硫醇,获得了各种各样的官能化环糊精。通过使用氟化烷硫醇,以优异的产率获得高度氟化的环糊精(高达56重量%的氟)。
Cyclodextrins are among the most popular host compounds in supramolecular chemistry. In this paper we describe a versatile approach to the multivalent functionalization of cyclodextrins by using photochemical thiol‐alkene addition reactions (“thiol‐ene click chemistry”). Starting from cyclodextrins allylated at the 2‐OH, 3‐OH and/or 6‐OH positions, a range of thiols could be introduced in good to excellent yields. By using alkanethiols substituted with hydroxy, carboxylic acid, ester, protected amine, and tetraethyleneglycol groups, a broad variety of functionalized cyclodextrins was obtained. By using fluorinated alkanethiols, highly fluorinated cyclodextrins (up to 56 wt.‐% of fluorine) were obtained in excellent yield.
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发表时间: 1998-12-03
影响因子: 7.3
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