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

Lucjan Strekowski, Maryam Hojjat, Steven E. Patterson, Alexander S. Kiselyov

Research output: Contribution to journalArticlepeer-review

19 Scopus citations

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.

Original languageEnglish (US)
Pages (from-to)1413-1416
Number of pages4
JournalJournal of Heterocyclic Chemistry
Volume31
Issue number6
DOIs
StatePublished - Jan 1 1994

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