Published June 23, 2020
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Thiosulfonylation of Unactivated Alkenes with Visible-Light Organic Photocatalysis
Creators
- 1. Division of Organic Synthesis, Department of Chemistry, University of Antwerp, Groenenborgerlaan 171, B-2020 Antwerp, Belgium
- 2. Biophysics and Biomedical Physics (BIMEF), Department of Chemistry, University of Antwerp, Universiteitsplein 1, B-2610 Antwerp, Belgium
- 3. Molecular Spectroscopy, Department of Chemistry, University of Antwerp, Groenenborgerlaan 171, B-2020 Antwerp, Belgium
Description
A metal-free method for the vicinal thiosulfonylation of unactivated alkenes with thiosulfonates using 9-mesityl-10-methylacridinium perchlorate as the photo-organocatalyst with visible-light irradiation has been developed. The method can be performed in dimethyl carbonate under air at room temperature and features a broad functional group compatibility. Metrics indicate the green potential of the developed versus the state-of-the-art methodologies. Mechanistic studies revealed no single electron transfer but involvement of an energy transfer from the excited photo-organocatalyst to thiosulfonate reactant, subsequently providing a sulfenyl and a sulfonyl radical via homolytic cleavage.
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- Cites
- Dataset: 10.5281/zenodo.4405208. (DOI)