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Multivalent Functionalization of Cyclodextrins by Photochemical Thiol‐Ene Addition Reaction
Author(s) -
Becker Maria M.,
Zeng Zhaoyang,
Ravoo Bart Jan
Publication year - 2013
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201300880
Subject(s) - chemistry , thiol , surface modification , alkene , ene reaction , click chemistry , supramolecular chemistry , amine gas treating , organic chemistry , reactivity (psychology) , yield (engineering) , fluorine , photochemistry , combinatorial chemistry , polymer chemistry , molecule , catalysis , medicine , materials science , alternative medicine , pathology , metallurgy
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.