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Catalytic 1,3-Difunctionalization via Oxidative C-C Bond Activation

Steven M. Banik, Katrina M. Mennie and Eric N. Jacobsen*

*Department of Chemistry & Chemical Biology, Harvard University, Cambridge, Massachusetts 02138, United States, Email: jacobsenchemistry.harvard.edu

S. M. Banik, K. M. Mennie, E. N. Jacobsen, J. Am. Chem. Soc., 2017, 139, 9152-9155.

DOI: 10.1021/jacs.7b05160 (free Supporting Information)


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Abstract

A general strategy for the 1,3-oxidation of cyclopropanes using aryl iodine(I-III) catalysis enables the synthesis of 1,3-difluorides, 1,3-fluoroacetoxylated products, 1,3-diols, 1,3-amino alcohols, and 1,3-diamines. These reactions make use of practical, commercially available reagents and can engage a variety of substituted cyclopropane substrates.

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Key Words

benzyl fluorides, alkyl fluorides, MCPBA


ID: J48-Y2017