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dc.contributor.authorBanik, Steven
dc.contributor.authorMennie, Katrina
dc.contributor.authorJacobsen, Eric
dc.date.accessioned2019-08-29T12:29:25Z
dc.date.issued2017-06-29
dc.identifier.citationBanik, Steven M., Katrina M. Mennie, and Eric N. Jacobsen. 2017. Catalytic 1,3-Difunctionalization via Oxidative C–C Bond Activation. Journal of the American Chemical Society 139, no. 27: 9152-9155.en_US
dc.identifier.issn0002-7863en_US
dc.identifier.issn1520-5126en_US
dc.identifier.urihttp://nrs.harvard.edu/urn-3:HUL.InstRepos:41275737*
dc.description.abstractElectronegative substituents arrayed in 1,3-relationships along saturated carbon frameworks can exert strong influence over molecular conformation due to dipole minimization effects. Simple and general methods for incorporation of such functional group relationships could thus provide a valuable tool for modulating molecular shape. Here, we describe a general strategy for the 1,3-oxidation of cyclopropanes using aryl iodine(I-III) catalysis, with emphasis on 1,3-difluorination reactions. These reactions make use of practical, commercially available reagents and can engage a variety of substituted cyclopropane substrates. Analysis of crystal and solution structures of several of the products reveal the consistent effect of 1,3-difluorides in dictating molecular conformation. The generality of the 1,3-oxidation strategy is demonstrated through the catalytic oxidative ring-opening of cyclopropanes for the synthesis of 1,3-fluoroacetoxylated products, 1,3-diols, 1,3-amino alcohols, and 1,3-diamines.en_US
dc.description.sponsorshipChemistry and Chemical Biologyen_US
dc.language.isoen_USen_US
dc.publisherAmerican Chemical Society (ACS)en_US
dc.relation.hasversionhttps://www.ncbi.nlm.nih.gov/pubmed/28622723en_US
dash.licenseMETA_ONLY
dc.titleCatalytic 1,3-Difunctionalization via Oxidative C–C Bond Activationen_US
dc.typeJournal Articleen_US
dc.description.versionProofen_US
dc.relation.journalJournal of the American Chemical Societyen_US
dash.depositing.authorJacobsen, Eric
dc.date.available2019-08-29T12:29:25Z
dash.workflow.commentsFAR2017en_US
dash.funder.nameNational Science Foundationen_US
dash.funder.awardGM043214en_US
dc.identifier.doi10.1021/jacs.7b05160
dc.source.journalJ. Am. Chem. Soc.
dash.source.volume139;27
dash.source.page9152-9155
dash.contributor.affiliatedMennie, Katrina
dash.contributor.affiliatedJacobsen, Eric


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