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Experimental and computational studies of trifluoromethylation of aromatic amines by the system trifluoroiodomethane‐zinc‐sulfur dioxide

1994; Wiley; Volume: 31; Issue: 6 Linguagem: Inglês

10.1002/jhet.5570310619

1943-5193

Lucjan Strękowski, Maryam Hojjat, Steven Patterson, Alexander S. Kiselyov,

Fluorine in Organic Chemistry

Abstract Several trifluoromethyl‐substituted aromatic and heteroaromatic amines have been obtained by the reactions of the corresponding amines with the title reagent system. Computational results provide rationalization for the observed regioselectivities and support a mechanism in which the electrophilic trifluoromethyl radicals interact with the aromatic ring at the sites with the greatest electron density of the HOMO orbitals, and then the resultant adducts are oxidized to cations. The products obtained are potential building blocks for a number of heterocyclic systems.