Angewandte Chemie · 2016 · 35 citations · 21 references
Natural SciencesChemical EngineeringChemistryCatalysisPhysical ChemistryReaction EngineeringHigh-throughput SynthesisPhotocatalysisPhotochemical SynthesisPhotochemistryContinuous-flow Photochemical SynthesisFluorination ProcessesPhotocatalytic SynthesisPhotochemical FunctionalizationPhotoredox CatalysisThroughputThroughput ImprovementVisible-light Photocatalysis
Abstract We report the first practical use of SF 6 as a fluorinating reagent in organic synthesis. Photoredox catalysis enables the in situ conversion of SF 6 , an inert gas, into an active fluorinating species by using visible light. Under these conditions, deoxyfluorination of allylic alcohols is effected with high chemoselectivity and is tolerant of a wide range of functional groups. Application of the methodology in a continuous‐flow setup achieves comparable yields to those obtained with a batch setup, while providing drastically increased material throughput of valuable allylic fluoride products.
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The Use of Gases in Flow Synthesis
Carl J. Mallia, Ian R. Baxendale · Organic Process Research & Development · 2015 · 357 citations · Full text