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Updated: Sep 7, 2025

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
Published on: August 16, 2018
Enolate SNAr of unactivated arenes via [(η6-arene)RuCp]+ intermediates
Luke J Williams1, Yunas Bhonoah2, James W Walton1
1Department of Chemistry, University of Durham, Lower Mountjoy, Durham, DH1 3LE, UK. james.walton@durham.ac.uk.
Abstract:
A series of complexes of the general formula [(η6-arene)RuCp][PF6] (where arene = aryl halides or nitroarenes) were synthesised and the arene ring was found to be reactive towards an intermolecular nucleophilic aromatic substitution (SNAr) reaction with a series of cyclic 1,3-diones. Competition experiments indicated that leaving group ability of the aryl halides and nitroarenes went in the order of F ≫ NO2 > Cl > Br. Following SNAr, the arene rings were liberated quantitatively via a rapid photolysis reaction (<15 min).
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