Gaseous SF(3)(+): An efficient electrophilic monofluorinating agent for five-membered heteroaromatic compounds |
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Authors: | Gozzo Ifa Eberlin |
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Institution: | Institute of Chemistry, State University of Campinas - UNICAMP, CP 6154, 13083-970 Campinas, SP Brazil. |
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Abstract: | Reactions of gaseous SF(3)(+) ions with furan, thiophene, pyrrole, and several of their alkyl derivatives were performed via MS(2) experiments and found to occur readily both by electron abstraction and F(+) transfer. Then, by performing MS(3) experiments, the F(+) transfer products-the protonated monofluorinated molecules-were mass-selected and deprotonated by a second reaction with a stronger base. F(+) transfer from gaseous SF(3)(+) followed by deprotonation promotes therefore C-H by C-F replacement in five-membered heteroaromatic compounds and the efficient gas-phase synthesis of their neutral monofluorinated derivatives. |
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