Abstract
The authors report a general room-temperature procedure for the direct, regioselective substitution of the hydroxy group in allylic, propargylic and benzylic alcohols with sulfonamides, carbamates and carboxamides, all of which are known to be relatively weak nucleophiles. A commercially available Bi(OTf)3/KPF6 catalytic system is used delivering the respective amides in moderate to excellent yields under mild reaction conditions. The definitive advantage of this method is the excellent generality, including the conversion of cyclic and acyclic, benzylic and non-benzylic allylic and even of tertiary propargylic alcohols and its regioselectivity - allylic alcohols have been found to be attacked in the sterically less hindered position, whereas in propargylic alcohols the nucleophile occupies the original position of the hydroxyl group.
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