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. 2024 Nov 18;63(47):e202412682.
doi: 10.1002/anie.202412682. Epub 2024 Oct 14.

Ligand-Enabled Gold-Catalyzed Cyanation of Organohalides

Anil Kumar  1 , Nandita Bhattacharya  1 , Manoj V Mane  2 , Nitin T Patil  1
Affiliations

Ligand-Enabled Gold-Catalyzed Cyanation of Organohalides

Anil Kumar et al. Angew Chem Int Ed Engl. .

Abstract

Herein, we disclose the first report on gold-catalyzed C(sp2)-CN cross-coupling reaction by employing a ligand-enabled Au(I)/Au(III) redox catalysis. This transformation utilizes acetone cyanohydrin as a nucleophilic cyanide source to convert simple aryl and alkenyl iodides into the corresponding nitriles. Combined experimental and computational studies highlighted the crucial role of cationic silver salts in activating the stable (P,N)-AuCN complex towards the oxidative addition of aryl iodides to subsequently generate key aryl-Au(III) cyanide complexes.

Keywords: C(sp2)-CN coupling; cross-coupling; gold; gold-cyanide; redox catalysis.

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