Journal
ACS CATALYSIS
Volume 10, Issue 15, Pages 8765-8779Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.0c02159
Keywords
Visible-light photocatalysis; Organic photocatalyst; Thiosulfonates; Difunctionalization; Energy Transfer
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Funding
- Hercules and the Francqui Foundation
- University of Antwerp (BOF doctoral scholarship)
- European Union's Horizon 2020 research and innovation program under the Marie Sklodowska-Curie Grant [813209, 792946]
- University of Antwerp (CASCH Excellence Center)
- Marie Curie Actions (MSCA) [792946] Funding Source: Marie Curie Actions (MSCA)
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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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