Unusual Fusion of α-Fluorinated Benzophenones under McMurry Reaction Conditions.

Chemistry

Department of Chemistry and Pharmacy, Organic Chemistry II, Friedrich-Alexander University Erlangen-Nuernberg, Nikolaus-Fiebiger Str. 10, 91058, Erlangen, Germany.

Published: February 2019

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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http://dx.doi.org/10.1002/chem.201805290DOI Listing

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