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. 2015 Jul 13;54(29):8533-7.
doi: 10.1002/anie.201503373. Epub 2015 Jun 9.

Catalytic Intramolecular Aminofluorination, Oxyfluorination, and Carbofluorination with a Stable and Versatile Hypervalent Fluoroiodine Reagent

Weiming Yuan  1 , Kálmán J Szabó  2
Affiliations

Catalytic Intramolecular Aminofluorination, Oxyfluorination, and Carbofluorination with a Stable and Versatile Hypervalent Fluoroiodine Reagent

Weiming Yuan et al. Angew Chem Int Ed Engl. .

Abstract

Application of a fluoroiodine analogue of the Togni reagent was studied in fluorocyclization reactions. In the presence of a transition-metal catalyst the applied fluoroiodine reagent can be used for aminofluorination, oxyfluorination, and carbofluorination reactions. The described procedure has a very broad synthetic scope for preparation of functionalized hetero- and isocyclic compounds having a tertiary fluorine substituent.

Keywords: copper; cyclizations; fluorine; heterocycles; homogeneous catalysis.

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Figures

Figure 1
Figure 1
Catalytic fluorocyclization reactions in this study. Ts= 4-toluenesulfonyl.
Figure 2
Figure 2
Proposed mechanism of the fluorocyclization reactions exemplified by the reaction of 2 m to afford 3 m (Table 2, entry 13).
See this image and copyright information in PMC

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