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3‐ tert ‐Butyl‐Substituted Cyclohexa‐1,4‐dienes as Isobutane Equivalents in the B(C 6 F 5 ) 3 ‐Catalyzed Transfer Hydro‐ tert ‐Butylation of Alkenes
Author(s) -
Keess Sebastian,
Oestreich Martin
Publication year - 2017
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201604397
Subject(s) - isobutane , carbocation , chemistry , borane , medicinal chemistry , alkyl , catalysis , boron , hydrocarbon , lewis acids and bases , organic chemistry
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.