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Abstract
Alkene difunctionalization is a very attractive tool in synthetic organic chemistry. Herein, we disclose an operationally and practically simple method to access 2-hydroxytrifluoroethylacetophenones from styrene derivatives via photoredox catalysis. This light-mediated transformation promotes the generation of the 1-hydroxy-2,2,2-trifluoroethyl carbon-centered radical as key synthon, which undergoes Giese addition with styrenes followed by a Kornblum oxidation process. The presented method is not only mild and cost-effective, but also utilizes an organic photocatalyst and DMSO as oxidant. Experimental investigations support the operative mechanism via net-neutral radical/polar crossover.
Original language | English |
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Pages (from-to) | 11682-11692 |
Number of pages | 11 |
Journal | Journal of Organic Chemistry |
Volume | 89 |
Issue number | 16 |
DOIs | |
Publication status | Published - 1 Aug 2024 |
Keywords
- Alkenes
- Catalysis
- Difunctionalization
- Trifluoromethyl ketones
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Dive into the research topics of 'Direct Synthesis of 2-Hydroxytrifluoroethylacetophenones via Organophotoredox-Mediated Net-Neutral Radical/Polar Crossover'. Together they form a unique fingerprint.Projects
- 2 Active
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EMERGENT (PER)FLUORINATION METHODS. PHOTOCATALYSIS
Vallribera Masso, A. (Principal Investigator), Pleixats Rovira, R. (Investigator), Granados Toda, A. (Investigator), Liu, M. Z. (Collaborator) & Tan, X. (Collaborator)
1/09/22 → 31/08/25
Project: Research Projects and Other Grants
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ORGANIC MOLECULES AND MATERIALS FOR CATALYTIC SUNLIGHT DRIVEN REACTIONS
Gimbert Suriñach, C. (Principal Investigator) & Gallego Gamo, A. (Collaborator)
1/09/22 → 31/08/25
Project: Research Projects and Other Grants