Enolate SNAr of unactivated arenes via [(η6-arene)RuCp]+ intermediates. Issue 80 (23rd June 2022)

• Record Type: Journal Article
• Authors: Williams, Luke J.; Bhonoah, Yunas; Walton, James W.
• Is Part Of: Chemical communications. Volume 58:Issue 80(2022)
• Page Start: 11240
• Page End: 11243
• Publication Date: 2022-06-23
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1039/d2cc02508f
• Languages: English
• ISSNs: 1359-7345

Abstract

Abstract : SN Ar of unactivated arenes with enolate nucleophiles is facilitated by π-coordination to Ru and subsequent product release by photolysis. Abstract : A series of complexes of the general formula [(η 6 -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 (SN Ar) 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 SN Ar, the arene rings were liberated quantitatively via a rapid photolysis reaction (<15 min).