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      Taming Super Lewis Acids for Catalysis: The Family of Ferrocene-Stabilized Silicon Cations

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            Abstract

            Tricoordinate silicon cations are exceptionally strong electron pair acceptors, so strong that they react with almost any σ and π basic molecule. In order to use such reactive intermediates in synthetic chemistry, Lewis acid catalysis in particular, we have designed intramolecularly stabilized silylium ions whose electron deficiency is attenuated by an adjacent, electron-rich ferrocenyl fragment. Here we wish to present the synthesis and structural characterization of these unique transition metal-stabilized silicon cations which reveal an unprecedented bonding situation different from its isoelectronic analogues. The potential of this motif is further highlighted in challenging Diels–Alder reactions, which are catalyzed at low temperatures with exceptional reaction rates and selectivities.

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            Conference
            ScienceOpen Posters
            ScienceOpen
            September 29 2014
            Author information
            https://orcid.org/0000-0003-3748-6609
            Article
            10.14293/P2199-8442.1.SOP-CHEM.PMUGH7.v1
            e65b6b6d-89a7-47c3-8b04-d8e750448c5b

            This work has been published open access under Creative Commons Attribution License CC BY 4.0 , which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. Conditions, terms of use and publishing policy can be found at www.scienceopen.com .

            ISOS XVII BERLIN 2014
            History

            Chemistry
            silicon, silylium ions, silicon cations, ferrocene, Lewis acids, Lewis acid catalysis, homogeneous catalysis, Diels-Alder reaction

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