Issue 19, 2019

Organic photoredox catalysis enabled cross-coupling of arenediazonium and sulfinate salts: synthesis of (un)symmetrical diaryl/alkyl aryl sulfones

Abstract

We disclose herein the first transition-metal- and external oxidant/reductant-free visible-light-mediated synthesis of (un)symmetrical diaryl/alkyl aryl sulfones from arenediazonium tetrafluoroborates and sodium sulfinates using eosin Y as an organic photoredox catalyst. The utilization of visible light as an inexpensive and ecosustainable energy source, operational simplicity, ambient temperature and clean reaction in aqueous acetonitrile are the salient features of the developed protocol. The desired sulfones were also synthesized via a one-pot, two-step process directly from anilines and sulfinate salts in good to excellent yields.

Graphical abstract: Organic photoredox catalysis enabled cross-coupling of arenediazonium and sulfinate salts: synthesis of (un)symmetrical diaryl/alkyl aryl sulfones

Supplementary files

Article information

Article type
Paper
Submitted
14 Apr 2019
Accepted
18 Apr 2019
First published
18 Apr 2019

Org. Biomol. Chem., 2019,17, 4761-4766

Organic photoredox catalysis enabled cross-coupling of arenediazonium and sulfinate salts: synthesis of (un)symmetrical diaryl/alkyl aryl sulfones

R. Chawla and L. D. S. Yadav, Org. Biomol. Chem., 2019, 17, 4761 DOI: 10.1039/C9OB00864K

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