Visible Light-Driven, Gold(I)-Catalyzed Preparation of Symmetrical (Hetero)biaryls by Homocoupling of Arylazo Sulfones

Lorenzo Di Terlizzi; Simone Scaringi; Carlotta Raviola; Riccardo Pedrazzani; Marco Bandini; Maurizio Fagnoni; Stefano Protti

doi:10.1021/acs.joc.2c00225

Visible Light-Driven, Gold(I)-Catalyzed Preparation of Symmetrical (Hetero)biaryls by Homocoupling of Arylazo Sulfones

J Org Chem. 2022 Apr 1;87(7):4863-4872. doi: 10.1021/acs.joc.2c00225. Epub 2022 Mar 22.

Authors

Lorenzo Di Terlizzi¹, Simone Scaringi^{1

2}, Carlotta Raviola¹, Riccardo Pedrazzani³, Marco Bandini³, Maurizio Fagnoni¹, Stefano Protti¹

Affiliations

¹ PhotoGreen Lab, Department of Chemistry, University of Pavia, Viale Taramelli 12, 27100 Pavia, Italy.
² Department of Organic Chemistry, University of Geneva, 30 quai Ernest Ansermet, 1211 Geneva, Switzerland.
³ Dipartimento di Chimica ″Giacomo Ciamician″, Alma Mater Studiorum-University of Bologna, Via Selmi 2, 40126 Bologna, Italy.

Abstract

The preparation of symmetrical (hetero)biaryls via arylazo sulfones has been successfully carried out upon visible light irradiation in the presence of PPh₃AuCl as the catalyst. The present protocol led to the efficient synthesis of a wide range of target compounds in an organic-aqueous solvent under photocatalyst-free conditions.