Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 362, Issue 4, Pages 760-764Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201901454
Keywords
Fluorine; sulfur; diethyl phosphonodifluoromethylthiolation reagent; radical pathway; synthetic methodologies
Categories
Funding
- INSA Rouen
- Rouen University
- CNRS
- EFRD
- Labex SynOrg [ANR-11-LABX-0029]
- Region Normandie (Crunch Network)
- Innovation Chimie Carnot (I2 C)
- European Research Council (ERC) under the European Union's Horizon 2020 research and innovation program [758710]
- Region Normandy
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In this manuscript, the synthesis of an original SCF2PO(OEt)(2)-containing reagent was depicted. Thanks to the unique properties of this newly-designed source, an unprecedented transformation with aldehydes was conducted under radical conditions, offering an access to value-added fluoroalkylthio compounds. Preliminary mechanistic studies were conducted and supported a radical reaction mechanism. Remarkably, thiol and disulfide derivatives turned out to be suitable coupling partners in a transition metal free transformation towards the synthesis of difficult-to-synthesize unsymmetrical disulfides. Finally, the difunctionalization of 4-phenyl-butene was investigated using this reagent.
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