Benzyl N-phenyl-2,2,2-trifluoroacetimidate: A new and stable reagent for O-benzylation

A new O-benzylation reagent, benzyl N-phenyl-2,2,2-trifluoroacetimidate, has been developed. It even reacts with sterically hindered alcohols and base-sensitive hydroxy esters to afford the corresponding benzyl ethers catalyzed by TMSOTf in 1,4-dioxane. This reagent was more stable than benzyl 2,2,2...

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Bibliographic Details
Published inChemistry letters Vol. 36; no. 8; pp. 992 - 993
Main Authors Okada, Yasunori, Ohtsu, Mamiko, Bando, Masafumi, Yamada, Hidetoshi
Format Journal Article
LanguageEnglish
Published TOKYO Chemical Soc Japan 05.08.2007
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
ALCOHOLS
TRIMETHYLSILYL TRIFLATE
TRICHLOROACETIMIDATE
ETHERS
ACID-CATALYZED BENZYLATION
ALKYLATION
GLYCOSYL
DONORS
EFFICIENT METHOD
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Summary:A new O-benzylation reagent, benzyl N-phenyl-2,2,2-trifluoroacetimidate, has been developed. It even reacts with sterically hindered alcohols and base-sensitive hydroxy esters to afford the corresponding benzyl ethers catalyzed by TMSOTf in 1,4-dioxane. This reagent was more stable than benzyl 2,2,2-trichloroacetimidate, a known benzylation reagent.
ISSN:0366-7022
1348-0715
DOI:10.1246/cl.2007.992