Photocatalytic Giese Addition of 1,4-Dihydroquinoxalin-2-ones to Electron-Poor Alkenes Using Visible Light

Jaume Rostoll-Berenguer; Gonzalo Blay; José R Pedro; Carlos Vila

doi:10.1021/acs.orglett.0c02953

Photocatalytic Giese Addition of 1,4-Dihydroquinoxalin-2-ones to Electron-Poor Alkenes Using Visible Light

Org Lett. 2020 Oct 16;22(20):8012-8017. doi: 10.1021/acs.orglett.0c02953. Epub 2020 Oct 1.

Authors

Jaume Rostoll-Berenguer¹, Gonzalo Blay¹, José R Pedro¹, Carlos Vila¹

Affiliation

¹ Departament de Quı́mica Orgànica, Facultat de Quı́mica, Universitat de València, Dr. Moliner 50, Burjassot, 46100 València, Spain.

PMID: 33000624
DOI: 10.1021/acs.orglett.0c02953

Abstract

The visible-light photoredox-catalyzed coupling of 1,4-dihydroquinoxalin-2-ones and Michael acceptors was achieved using Ru(bpy)₃Cl₂ as the photocatalyst and (PhO)₂PO₂H as an additive. The optimized reaction conditions provide a good yield for the radical conjugate addition products (44 examples) with a wide range of structurally different Michael acceptors. A gram scale reaction using sunlight irradiation is also described. Furthermore, several transformations were carried out with the Giese addition products.