PERFLUOROALKYLATION REACTIONS OF (HETERO)ARENES

BARAJA VALLEJO SEBASTIAN; BONESI SERGIO M; POSTIGO J. ALBERTO

RSC Advances

Royal Society of Chemistry

Año: 2015 vol. 5 p. 62498 - 62518

2046-2069

PERFLUOROALKYLATION REACTIONS OF (HETERO)ARENESSebastián Barata-Vallejo, a Sergio M. Bonesi*,b and Al Postigo*,aa.-Departamento de Química Orgánica, Facultad de Farmacia y Bioquímica, Universidad de Buenos Aires-Junín 954 CP 1113-Buenos Aires-Argentinab.-Departamento de Química Orgánica, CIHIDECAR-CONICET, Pabellón II, 3er piso, Ciudad Universitaria, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, 1428, Buenos Aires, ArgentinaAbstractPerfluoroalkylation reactions of arenes have not been the subject of intense studies as has been the case for the trifluoromethylation reactions of aromatics. However, the new synthetic methods proposed for achieving homolytic aromatic substitution reactions with perfluorolkyl moieties have begun to claim a relevant role in functionalization reactions, as revealed by the interesting properties of arenes with large perfluoroalkyl chains. Methods for achieving Ar-Rf bonding reactions can be classified into thermal and photochemical, which can in turn make use of transition metals or be non-metal catalyzed. Reactions are mainly radical in nature. Radical methods for introducing Rf moieties into arenes have resulted as being the most popular, and interesting examples have been documented. IndexIntroduction1.-Thermal methods1.1.-Transition metal-free thermal perfluoroalkylation methods1.2.-Transition-metal catalyzed or activated thermal perfluoroalkylation of arenes2.-Photoinduced methods for perfluoroalkylation of arenes2.1.-Transition metal-free photoorganocatalyzed perfluoroalkylation reactions of arenes2.2.-Transition metal photocatalyzed perfluoroalkylation of arenes3.-Conclusions4.-References