Literature DB >> 27775187

3-tert-Butyl-Substituted Cyclohexa-1,4-dienes as Isobutane Equivalents in the B(C6 F5 )3 -Catalyzed Transfer Hydro-tert-Butylation of Alkenes.

Sebastian Keess1, Martin Oestreich1.   

Abstract

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.
© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  Lewis acids; alkenes; boron; carbocations; hydroalkylation

Year:  2016        PMID: 27775187     DOI: 10.1002/chem.201604397

Source DB:  PubMed          Journal:  Chemistry        ISSN: 0947-6539            Impact factor:   5.236


  1 in total

1.  Lewis Acid Catalyzed Transfer Hydromethallylation for the Construction of Quaternary Carbon Centers.

Authors:  Johannes C L Walker; Martin Oestreich
Journal:  Angew Chem Int Ed Engl       Date:  2019-09-12       Impact factor: 15.336

  1 in total

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