Unusual Fusion of α-Fluorinated Benzophenones under McMurry Reaction Conditions |
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Authors: | Vladimir Akhmetov Mikhail Feofanov Vitaliy Ioutsi Frank Hampel Konstantin Amsharov |
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Institution: | 1. Department of Chemistry and Pharmacy, Organic Chemistry II, Friedrich-Alexander University Erlangen-Nuernberg, Nikolaus-Fiebiger Str. 10, 91058 Erlangen, Germany;2. Endocrinology Research Centre, 117036 Moscow, Dmitriya Ul'yanova str. 11, Russia |
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Abstract: | 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. |
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Keywords: | anthracene arenes C−F chemistry McMurry reaction organic chemistry |
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