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

Sebastiaan A. van den Berg; Raoul A.M. Frijns; Tom Wennekes; Han Zuilhof

doi:10.1556/1846.2015.00006

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Journal of Flow Chemistry

Volume/Issue:: Volume 5: Issue 2

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

Authors:

Sebastiaan A. van den Berg

Sebastiaan A. van den Berg Wageningen University, Dreijenplein 8, 6703 HB, Wageningen, The Netherlands

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Raoul A.M. Frijns

Raoul A.M. Frijns Wageningen University, Dreijenplein 8, 6703 HB, Wageningen, The Netherlands

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Tom Wennekes

Tom Wennekes Wageningen University, Dreijenplein 8, 6703 HB, Wageningen, The Netherlands

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, and

Han Zuilhof

Han Zuilhof Wageningen University, Dreijenplein 8, 6703 HB, Wageningen, The Netherlands
King Abdulaziz University, Jeddah, Saudi Arabia

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Pages:: 95–100

Online Publication Date:: Jun 2015

Publication Date:: 01 Jun 2015

Article Category:: Research Article

DOI:: https://doi.org/10.1556/1846.2015.00006

Keywords:: catalysis; continuous flow; packed bed; silyl ether; alcohol protection and deprotection

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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.

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Journal of Flow Chemistry A Journal of the Flow Chemistry Society

Print ISSN:: 2062-249X

Online ISSN:: 2063-0212

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Journal of Flow Chemistry
Language	English
Size	A4
Year of Foundation	2011
Volumes per Year	1
Issues per Year	4
Founder	Áramlásos Kémiai Tudományos Társaság
Founder's Address	H-1031 Budapest, Hungary Záhony utca 7.
Publisher	Akadémiai Kiadó Springer Nature Switzerland AG
Publisher's Address	H-1117 Budapest, Hungary 1516 Budapest, PO Box 245. CH-6330 Cham, Switzerland Gewerbestrasse 11
Responsible Publisher	Chief Executive Officer, Akadémiai Kiadó
ISSN	2062-249X (Print)
ISSN	2063-0212 (Online)