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
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 perfluoro...
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Published in | Chemical science (Cambridge) Vol. 8; no. 9; pp. 6066 - 6070 |
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Main Authors | , , |
Format | Journal Article |
Language | English |
Published |
Royal Society of Chemistry
05.06.2017
|
Subjects | |
Online Access | Get full text |
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Abstract | 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. |
---|---|
AbstractList | 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. |
Author | Ngai, Ming-Yu Lee, Johnny W. Spiegowski, Dominique N. |
AuthorAffiliation | b Institute of Chemical Biology and Drug Discovery , Stony Brook University , Stony Brook , New York 11794-3400 , USA a Department of Chemistry , Stony Brook University , Stony Brook , New York 11794-3400 , USA . Email: ming-yu.ngai@stonybrook.edu |
AuthorAffiliation_xml | – name: a Department of Chemistry , Stony Brook University , Stony Brook , New York 11794-3400 , USA . Email: ming-yu.ngai@stonybrook.edu – name: b Institute of Chemical Biology and Drug Discovery , Stony Brook University , Stony Brook , New York 11794-3400 , USA |
Author_xml | – sequence: 1 givenname: Johnny W. surname: Lee fullname: Lee, Johnny W. organization: Department of Chemistry , Stony Brook University , Stony Brook , New York 11794-3400 , USA . Email: Institute of Chemical Biology and Drug Discovery , Stony Brook University , Stony Brook , New York 11794-3400 , USA – sequence: 2 givenname: Dominique N. surname: Spiegowski fullname: Spiegowski, Dominique N. organization: Department of Chemistry , Stony Brook University , Stony Brook , New York 11794-3400 , USA . Email: Institute of Chemical Biology and Drug Discovery , Stony Brook University , Stony Brook , New York 11794-3400 , USA – sequence: 3 givenname: Ming-Yu surname: Ngai fullname: Ngai, Ming-Yu organization: Department of Chemistry , Stony Brook University , Stony Brook , New York 11794-3400 , USA . Email: Institute of Chemical Biology and Drug Discovery , Stony Brook University , Stony Brook , New York 11794-3400 , USA |
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Snippet | Synthesis of perfluoroalkoxylated (hetero)arenes (Ar–OR
F
) from readily available perfluoroalkyl iodides (R
F
–I) through photocatalytic selective O–R
F
bond... |
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SubjectTerms | Chemistry |
Title | 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 |
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