Copper Catalyzed β‑Difluoroacetylation of Dihydropyrans and Glycals by Means of Direct C–H Functionalization

A copper catalyzed direct functionalization of dihydropyrans and glycals has been developed. This method affords a new and straightforward access to C-2-CF2 dihydropyrans and glycosides in a single step starting from readily available starting materials. This new copper based catalytic system, proba...

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Bibliographic Details
Published in:Organic letters 2013-07, Vol.15 (13), p.3428-3431
Main Authors: Belhomme, Marie-Charlotte, Poisson, Thomas, Pannecoucke, Xavier
Format: Article
Language:English
Subjects:
Catalysis
Chemical Sciences
Copper - chemistry
Glycosides - chemistry
Hydrocarbons, Fluorinated - chemistry
Hydrogen Bonding
Molecular Structure
Organic chemistry
Pyrans - chemistry
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Summary:A copper catalyzed direct functionalization of dihydropyrans and glycals has been developed. This method affords a new and straightforward access to C-2-CF2 dihydropyrans and glycosides in a single step starting from readily available starting materials. This new copper based catalytic system, probably involving a Cu(III) species as supported by experiments, allows the formation of the valuable fluorinated glycosides in good yields.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol401483j