Photocatalytic Decarboxylative Coupling of Aliphatic N‐Hydroxyphthalimide Esters with Bromopolyfluorobenzene

We describe a decarboxylative coupling reaction of N‐hydroxyphthalimide esters with bromopolyfluorobenzene enabled by the synergetic action of Hantzsch ester, photoredox catalyst, and nickel catalyst. This method readily converts primary and secondary alkyl carboxylic acids into the corresponding po...

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Bibliographic Details
Published inAdvanced synthesis & catalysis Vol. 365; no. 6; pp. 854 - 859
Main Authors Tao, Maoling, Zeng, Lin‐Yuan, Li, Weipiao, Pu, Guoliang, Jia, Jia, Yao, Qiuli, Li, Xuefei, He, Chun‐Yang
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 21.03.2023
Wiley Subscription Services, Inc
Subjects
alkylation
Amino acids
Carboxylic acids
Catalysts
Chemistry
Chemistry, Applied
Chemistry, Organic
Coupling
Coupling (molecular)
Esters
Functional groups
nickel catalyzed
photocatalysis
Photoredox catalysis
Physical Sciences
polyfluoroaryl
Science & Technology
ACTIVATION
DESIGN
ELECTRON-DEFICIENT POLYFLUOROARENES
C-H ALLYLATION
ARYLATION
nickel catalyzed
RADICAL GENERATION
METALLAPHOTOREDOX CATALYSIS
DIRECT OLEFINATION
alkylation
photocatalysis
polyfluoroaryl
FLUORINATED AMINO-ACIDS
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Summary:We describe a decarboxylative coupling reaction of N‐hydroxyphthalimide esters with bromopolyfluorobenzene enabled by the synergetic action of Hantzsch ester, photoredox catalyst, and nickel catalyst. This method readily converts primary and secondary alkyl carboxylic acids into the corresponding polyfluoroaryl compounds with broad scope and excellent functional group compatibility. The practicality of this method was further demonstrated by the direct modification of amino acids and biologically active molecules
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.202201279