Search

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. [ABSTRACT FROM AUTHOR]