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Continuous-Flow Alcohol Protection and Deprotection Reactions Catalyzed by Silica-Supported Sulfonic Acid

Continuous-Flow Alcohol Protection and Deprotection Reactions Catalyzed by Silica-Supported... Alcohol protection and deprotection reactions, catalyzed by solid-supported sulfonic acid, have been investigated under continuous-flow conditions. Primary, secondary, benzylic and phenolic alcohols can be protected under these conditions by tetrahydropyranyl and several silyl ether moieties, generating synthetically useful amounts of material in short time. Furthermore, the described setup can be used to deprotect protected alcohols and be used in selective protection reactions. Because the solid-supported acid catalyst is continually reused in a packed-bed approach, workup is greatly simplified and in most cases only solvent removal is necessary, while reaching high turn-over numbers.[graphic not available: see fulltext] http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Journal of Flow Chemistry Springer Journals

Continuous-Flow Alcohol Protection and Deprotection Reactions Catalyzed by Silica-Supported Sulfonic Acid

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Publisher
Springer Journals
Copyright
Copyright © Akadémiai Kiadó 2015
ISSN
2062-249X
eISSN
2063-0212
DOI
10.1556/1846.2015.00006
Publisher site
See Article on Publisher Site

Abstract

Alcohol protection and deprotection reactions, catalyzed by solid-supported sulfonic acid, have been investigated under continuous-flow conditions. Primary, secondary, benzylic and phenolic alcohols can be protected under these conditions by tetrahydropyranyl and several silyl ether moieties, generating synthetically useful amounts of material in short time. Furthermore, the described setup can be used to deprotect protected alcohols and be used in selective protection reactions. Because the solid-supported acid catalyst is continually reused in a packed-bed approach, workup is greatly simplified and in most cases only solvent removal is necessary, while reaching high turn-over numbers.[graphic not available: see fulltext]

Journal

Journal of Flow ChemistrySpringer Journals

Published: Apr 30, 2015

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