FeCl3-catalyzed aminohalogenation of arylmethylenecyclopropanes and arylvinylidenecyclopropanes and corresponding mechanistic studies

Qingjiang Li, Min Shi, Cody Timmons, Guigen Li

Research output: Contribution to journalArticlepeer-review

76 Scopus citations

Abstract

The aminochlorination of methylenecyclopropanes (MCPs) 1 and vinylidenecyclopropanes (VCPs) has been explored with use of FeCl3 (20 mol %) as a Lewis acid catalyst in acetonitrile under convenient mild conditions. The stereochemistry has been unambiguously confirmed by X-ray structural analysis. The aziridinium-based mechanism, accounting for both regio- and stereoselectivity, has been carefully studied. A linear free-energy relationship study of this reaction confirms consistency with the Hammet equation.

Original languageEnglish
Pages (from-to)625-628
Number of pages4
JournalOrganic Letters
Volume8
Issue number4
DOIs
StatePublished - Feb 16 2006

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