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

Qingjiang Li; Min Shi; Cody Timmons; Guigen Li

doi:10.1021/ol052806f

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

Qingjiang Li, Min Shi, Cody Timmons, Guigen Li

Chemistry and Biochemistry

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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 language	English
Pages (from-to)	625-628
Number of pages	4
Journal	Organic Letters
Volume	8
Issue number	4
DOIs	https://doi.org/10.1021/ol052806f
State	Published - Feb 16 2006

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title = "FeCl3-catalyzed aminohalogenation of arylmethylenecyclopropanes and arylvinylidenecyclopropanes and corresponding mechanistic studies",

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.",

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T1 - FeCl3-catalyzed aminohalogenation of arylmethylenecyclopropanes and arylvinylidenecyclopropanes and corresponding mechanistic studies

AU - Li, Qingjiang

AU - Shi, Min

AU - Timmons, Cody

AU - Li, Guigen

PY - 2006/2/16

Y1 - 2006/2/16

N2 - 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.

AB - 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.

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U2 - 10.1021/ol052806f

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JO - Organic Letters

JF - Organic Letters

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ER -

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

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