Journal
TETRAHEDRON
Volume 76, Issue 51, Pages -Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2020.131153
Keywords
Trifluoromethylthiolation; Fluorine chemistry; Visible light; Remote position; C(sp(3))-H bond functionalization
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Funding
- Normandie Universite (NU)
- Region Normandie
- Centre National de la Recherche Scientifique (CNRS)
- Universite de Rouen Normandie (URN)
- INSA Rouen Normandie
- Labex SynOrg [ANR-11-LABX-0029]
- Innovation Chimie Carnot (I2C)
- European Research Council (ERC) under the European Union's Horizon 2020 research and innovation programme [758710]
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An unprecedented remote and regioselective trifluoromethylthiolation reaction of alcohols was developed. Under mild conditions, a panel of free-alcohols was selectively functionalized with TolSO(2)SCF(3) reagent as the SCF 3 source in the presence of hypervalent iodide (PIDA) under blue light irradiation. This approach offered an operationally simple tool for the construction of a challenging C(sp(3))-SCF3 bond at the delta-position of an alcohol by C(sp(3))-H bond functionalization. Initial mechanistic studies suggested a radical pathway. (C) 2020 Elsevier Ltd. All rights reserved.
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