Selective C–O bond formation via a photocatalytic radical coupling strategy: access to perfluoroalkoxylated (ORF) arenes and heteroarenes† †Electronic supplementary information (ESI) available. See DOI: 10.1039/c7sc01684k Click here for additional data file

• Published in: Chemical science (Cambridge) Vol. 8; no. 9; pp. 6066 - 6070
• Main Authors: Lee, Johnny W., Spiegowski, Dominique N., Ngai, Ming-Yu
• Format: Journal Article
• Language: English
• Published: Royal Society of Chemistry 05.06.2017
• Subjects: Chemistry
• ISSN: 2041-6520; 2041-6539
• DOI: 10.1039/c7sc01684k

Synthesis of perfluoroalkoxylated (hetero)arenes (Ar–OR F ) from readily available perfluoroalkyl iodides (R F –I) through photocatalytic selective O–R F bond formation. 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 F I) 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.