Selective C-O bond formation via a photocatalytic radical coupling strategy: access to perfluoroalkoxylated (ORF) arenes and heteroarenes

Development of an efficient process that employs commercially available and cost effective reagents for the synthesis of perfluoroalkoxylated aromatic compounds (Ar-ORF) remains a daunting challenge in organic synthesis. Herein, we report the first catalytic protocol using readily available perfluor...

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Published inChemical science (Cambridge) Vol. 8; no. 9; pp. 6066 - 6070
Main Authors Lee, Johnny W., Spiegowski, Dominique N., Ngai, Ming-Yu
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 01.09.2017
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
MEDICINAL CHEMISTRY
ORGANIC-SYNTHESIS
HYDROXYLAMINES
OCF3 MIGRATION
PHENOLS
CATALYZED SYNTHESIS
ALPHA-FLUORINATED ETHERS
THIOETHERS
PERFLUOROALKYLATION
ARYL TRIFLUOROMETHYL ETHERS
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Summary:Development of an efficient process that employs commercially available and cost effective reagents for the synthesis of perfluoroalkoxylated aromatic compounds (Ar-ORF) remains a daunting challenge in organic synthesis. Herein, we report the first catalytic protocol using readily available perfluoroalkyl iodides (REI) and N-(hetero)aryl-N-hydroxylamides to access a wide range of perfluoroalkoxylated (hetero)arenes. Mild reaction conditions allow for selective O-R-F bond formation over a broad substrate scope and are tolerant of a wide variety of functional groups. Mechanistic studies suggest the formation and recombination of persistent N-hydroxyl radicals and transient R-F radicals under photocatalytic reaction conditions to generate N-ORF compounds that rearrange to afford the desired products.
Bibliography:NIH RePORTER
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ISSN:2041-6520
2041-6539
DOI:10.1039/c7sc01684k