Ligand-Enabled Gold-Catalyzed Cyanation of Organohalides

Anil Kumar; Nandita Bhattacharya; Manoj V Mane; Nitin T Patil

doi:10.1002/anie.202412682

Ligand-Enabled Gold-Catalyzed Cyanation of Organohalides

Angew Chem Int Ed Engl. 2024 Nov 18;63(47):e202412682. doi: 10.1002/anie.202412682. Epub 2024 Oct 14.

Authors

Anil Kumar¹, Nandita Bhattacharya¹, Manoj V Mane², Nitin T Patil¹

Affiliations

¹ Department of Chemistry, Indian Institute of Science Education and Research Bhopal, Bhopal Bypass Road, Bhauri, Bhopal, 462 066, India.
² Centre for Nano and Material Sciences, Jain (Deemed-to-be University), Jain Global Campus Kanakapura, Bangalore, Karnataka, 562112, India.

PMID: 39129346
DOI: 10.1002/anie.202412682

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.