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

Autor:	Lee JW; Department of Chemistry , Stony Brook University , Stony Brook , New York 11794-3400 , USA . Email: ming-yu.ngai@stonybrook.edu.; Institute of Chemical Biology and Drug Discovery , Stony Brook University , Stony Brook , New York 11794-3400 , USA., Spiegowski DN; Department of Chemistry , Stony Brook University , Stony Brook , New York 11794-3400 , USA . Email: ming-yu.ngai@stonybrook.edu.; Institute of Chemical Biology and Drug Discovery , Stony Brook University , Stony Brook , New York 11794-3400 , USA., Ngai MY; Department of Chemistry , Stony Brook University , Stony Brook , New York 11794-3400 , USA . Email: ming-yu.ngai@stonybrook.edu.; Institute of Chemical Biology and Drug Discovery , Stony Brook University , Stony Brook , New York 11794-3400 , USA.
Jazyk:	angličtina
Zdroj:	Chemical science [Chem Sci] 2017 Sep 01; Vol. 8 (9), pp. 6066-6070. Date of Electronic Publication: 2017 Jun 05.
DOI:	10.1039/c7sc01684k
Abstrakt:	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.
Databáze:	MEDLINE
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