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Relative Rate Profiles of Functionalized Iodoarene Catalysts for Iodine(III) Oxidations

Timothy R. Lex, Maria I. Swasy and Daniel C. Whitehead*

*Department of Chemistry, Clemson University, Clemson, South Carolina 29634, United States, Email: dwhitehclemson.edu

T. R. Lex, M. I. Swasy, D. C. Whitehead, J. Org. Chem., 2015, 80, 12234-12243.

DOI: 10.1021/acs.joc.5b02129 (free Supporting Information)


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Abstract

The reactivity of iodoarene amide catalysts in the α-oxytosylation of propiophenone is influenced by steric and electronic properties. A very reactive meta-substituted benzamide catalyst was employed in the α-oxytosylation of a series of substituted propiophenones to provide α-tosyloxy ketones in excellent isolated yield.

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Key Words

hydroxy ketones, hypervalent iodone compounds, MCPBA, organocatalysis


ID: J42-Y2015