4.7 Article

Bronsted acid-catalyzed nucleophilic substitution of alcohols

Journal

ADVANCED SYNTHESIS & CATALYSIS
Volume 348, Issue 14, Pages 1841-1845

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.200606183

Keywords

alcohols; C-C coupling; nucleophilic substitution; supported catalysts; synthetic methods

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Simple Bronsted acids such as p-toluenesulfonic acid monohydrate (PTS) or polymer-bound p-toluenesulfonic acid efficiently catalyze the direct nucleophilic substitution of the hydroxy group of allylic and benzylic alcohols with a large variety of carbon- and heteroatom-centered nucleophiles. Reaction conditions are mild, the process is conducted under an atmosphere of air without the need for dried solvents, and water is the only side product of the reaction.

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