Selective C-O bond formation via a photocatalytic radical coupling strategy: access to perfluoroalkoxylated (ORF) arenes and heteroarenesElectronic supplementary information (ESI) available. See DOI: 10.1039/c7sc01684k
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 perflu...
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Format | Journal Article |
Language | English |
Published |
21.08.2017
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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
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.
Synthesis of perfluoroalkoxylated (hetero)arenes (Ar-OR
F
) from readily available perfluoroalkyl iodides (R
F
-I) through photocatalytic selective O-R
F
bond formation. |
---|---|
AbstractList | 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.
Synthesis of perfluoroalkoxylated (hetero)arenes (Ar-OR
F
) from readily available perfluoroalkyl iodides (R
F
-I) through photocatalytic selective O-R
F
bond formation. |
Author | Spiegowski, Dominique N Ngai, Ming-Yu Lee, Johnny W |
AuthorAffiliation | Department of Chemistry Stony Brook University Institute of Chemical Biology and Drug Discovery |
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Title | Selective C-O bond formation via a photocatalytic radical coupling strategy: access to perfluoroalkoxylated (ORF) arenes and heteroarenesElectronic supplementary information (ESI) available. See DOI: 10.1039/c7sc01684k |
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