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

ABSTRACT: Development of an efficient process that employs commercially available and cost effective reagents for the synthesis of perfluoroalkoxylated aromatic compounds (Ar-OR_F) remains a daunting challenge in organic synthesis. Herein, we report the first catalytic protocol using readily available perfluoroalkyl iodides (R_FI) 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-OR_F compounds that rearrange to afford the desired products.

SUBMITTER: Lee JW

PROVIDER: S-EPMC5625593 | biostudies-literature | 2017 Sep

REPOSITORIES: biostudies-literature

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

Lee Johnny W JW Spiegowski Dominique N DN Ngai Ming-Yu MY

Chemical science 20170605 9

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 (RFI) and N-(hetero)aryl-N-hydroxylamides to access a wide range of perfluoroalkoxylated (hetero)arenes. Mild reaction conditions allow for selective ...[more]

PMID: 28989637

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