Issue 11, 2014

Formal fluorine atom transfer radical addition: silver-catalyzed carbofluorination of unactivated alkenes with ketones in aqueous solution

Abstract

In this article, we report the first examples of carbofluorination of unactivated alkenes. Under catalysis by AgNO3, the reactions of unactivated alkenes with Selectfluor reagent and active methylene compounds such as acetoacetates or 1,3-dicarbonyls in CH2Cl2–H2O–HOAc solution afforded the corresponding three-component condensation products under mild conditions. Furthermore, with the promotion of NaOAc, the AgOAc-catalyzed carbofluorination of various unactivated alkenes with Selectfluor and acetone proceeded smoothly in aqueous solution at 50 °C. The carbofluorination was efficient and highly regioselective, and enjoyed a broad substrate scope and wide functional group compatibility. These formal fluorine atom transfer radical addition reactions provide a convenient entry to structurally divergent, polyfunctional organofluorine compounds as versatile synthetic intermediates.

Graphical abstract: Formal fluorine atom transfer radical addition: silver-catalyzed carbofluorination of unactivated alkenes with ketones in aqueous solution

Supplementary files

Article information

Article type
Research Article
Submitted
26 Way 2014
Accepted
12 Xim 2014
First published
13 Xim 2014

Org. Chem. Front., 2014,1, 1299-1305

Author version available

Formal fluorine atom transfer radical addition: silver-catalyzed carbofluorination of unactivated alkenes with ketones in aqueous solution

L. Zhu, H. Chen, Z. Wang and C. Li, Org. Chem. Front., 2014, 1, 1299 DOI: 10.1039/C4QO00256C

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