Electrophilic trifluoromethylation reagents 1 and 2 have become quite popular since their report in 2006 by our group, as evidenced by numerous reports concerned with their applications in organofluorine chemistry.1,2 More recently, we developed a series of functionalized tetrafluoroethylating reagents 3 and 4 based on the same hypervalent iodine core (Figure 1).3 Reagents 3 and 4 show comparable reactivity towards a number of different nucleophiles as 1 and 2. Figure 1. Electrophilic trifluoromethylation and fluoroalkylation reagents 1-4. While exploring the reactivity of 3 and 4, we found that their application is not limited only to the simple transfer of the fluoroalkyl group, but that the functionality (FG) can also participate itself in a reaction. Indeed, reagents bearing a N-heteroaromatic substituent (e.g. imidazole) undergo a copper-catalyzed tandem fluoroalkylation-cyclization with alkenes, alkynes, and allenes, yielding tetrafluorinated tetrahydroimidazopyridines, some of which are shown in Figure 2.4,5 Figure 2. a Copper-Catalyzed tandem fluoroalkylation-cyclization. b Complex heterocyclic products. This reaction could be extended to a series of reagents bearing further functional groups, undergoing C-H activation;5 giving access to complex cyclic compounds of potential biological interest (Figure 3).6 References (1) Charpentier, J.; Früh, N.; Togni, A. Chem. Rev. 2015, 115, 650. (2) Früh, N.; Charpentier, J.; Togni, A.; Springer Berlin Heidelberg: 2015. (3) Matoušek, V.; Václavík, J.; Togni, A.; Beier, P., submitted for publication. (4) Charpentier, J.; Früh, N.; Foser, S.; Togni, A., manuscript in preparation. (5) Früh, N.; Calvo, R.; Charpentier, J.; Foser, S.; Togni, A., unpublished results. (6) Granier, T.; Panday, N.; Vasella, A. Helv. Chim. Acta 1997, 80, 979.

Synthesis of complex fluorinated heterocycles

251st National Meeting (2016)

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