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Unusual Fusion of α‐Fluorinated Benzophenones under McMurry Reaction Conditions
Author(s) -
Akhmetov Vladimir,
Feofanov Mikhail,
Ioutsi Vitaliy,
Hampel Frank,
Amsharov Konstantin
Publication year - 2019
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.201805290
Subject(s) - benzophenone , domino , fluorine , chemistry , photochemistry , bond cleavage , fusion , cleavage (geology) , condensation , transformation (genetics) , combinatorial chemistry , organic chemistry , materials science , thermodynamics , physics , catalysis , linguistics , philosophy , fracture (geology) , composite material , biochemistry , gene
By exposure of α‐fluorinated benzophenones to McMurry reaction conditions, we have observed the remarkable formation of 9,10‐diphenylanthracene derivatives. This unexpected transformation necessitates the cleavage of the exceptionally stable aromatic C−F bond under mild McMurry conditions. In this work, the condensation of several related fluorinated benzo‐ and acetophenones has been investigated, which allow us to propose a domino‐like fusion mechanism for this unusual transformation. The scope and limitations of the fluorine‐promoted benzophenone fusion are subsequently discussed.