A visible-light-induced, metal-free bis-arylation of 2,5-dichlorobenzoquinone

Pieterjan Winant; Wim Dehaen

doi:10.3762/bjoc.17.149

A visible-light-induced, metal-free bis-arylation of 2,5-dichlorobenzoquinone

Beilstein J Org Chem. 2021 Sep 6:17:2315-2320. doi: 10.3762/bjoc.17.149. eCollection 2021.

Authors

Pieterjan Winant¹, Wim Dehaen¹

Affiliation

¹ Molecular Design and Synthesis, Department of Chemistry, KU Leuven, Celestijnenlaan 200F, 3001 Leuven, Belgium.

Abstract

A metal-free protocol for the direct bis-arylation of 2,5-dichlorobenzoquinone with aryldiazonium salts is reported. The reactive salts are generated in situ and converted to radicals through irradiation with visible light. Reaction products precipitate from the solvent, eliminating the need for purification and thus providing a novel green method for the synthesis of versatile bis-electrophiles.

Keywords: Green Chemistry; Meerwein arylation; benzoquinone; diazonium salts; photoredox.

Grants and funding

We thank the KU Leuven (Project C14/19/78) and the FWO-Vlaanderen (bilateral project G0F6619N) for financial support. Mass spectrometry was made possible by the support of the Hercules Foundation of the Flemish Government (grant 20100225-7).