Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 23, Issue 25, Pages 5925-5928Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201604397
Keywords
alkenes; boron; carbocations; hydroalkylation; Lewis acids
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Funding
- Deutsche Forschungsgemeinschaft [Oe 249/11-1]
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Cyclohexa-1,4-dienes with a tert-butyl group at C3 are shown to function as isobutane equivalents when activated by the strong boron Lewis acid tris(pentafluorophenyl)borane. The hitherto unprecedented transfer hydro-tert-butylation from one unsaturated hydrocarbon to another is achieved with 1,1-diarylalkenes as substrates, thereby presenting itself as a new way of incorporating tertiary alkyl groups into carbon frameworks. Transient carbocation intermediates give rise to competing reaction pathways that could not be fully suppressed.
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