Perfluoroalkylation of Unactivated Alkenes with Acid Anhydrides as the Perfluoroalkyl Source

An efficient perfluoroalkylation of unactivated alkenes with perfluoro acid anhydrides was developed. Copper salts play a crucial role as a catalyst to achieve allylic perfluoroalkylation with the in situ generated bis(perfluoroacyl) peroxides. Furthermore, carboperfluoroalkylation of alkene bearing...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2016-07, Vol.55 (30), p.8740-8743
Main Authors: Kawamura, Shintaro, Sodeoka, Mikiko
Format: Article
Language:English
Subjects:
alkenes
copper
homogeneous catalysis
perfluoroalkylation
peroxide
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Summary:An efficient perfluoroalkylation of unactivated alkenes with perfluoro acid anhydrides was developed. Copper salts play a crucial role as a catalyst to achieve allylic perfluoroalkylation with the in situ generated bis(perfluoroacyl) peroxides. Furthermore, carboperfluoroalkylation of alkene bearing an aromatic ring at an appropriate position on the carbon side chain was found to proceed under metal‐free conditions to afford carbocycles or heterocycles bearing a perfluoroalkyl group. This method, which makes use of readily available perfluoroalkyl sources, offers a convenient and powerful tool for introducing a perfluoroalkyl group onto an sp3 carbon to construct synthetically useful skeletons. F for effective: Perfluoroalkylation of unactivated alkenes with perfluoro acid anhydrides as the perfluoroalkyl source was achieved. A copper catalyst enabled efficient allylic perfluoroalkylation with in situ generated diacyl peroxide. In addition, alkenes bearing an aromatic ring at an appropriate position on the carbon side chain afforded carboperfluoroalkylation products under metal‐free conditions.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201604127