Copper-Mediated Synthesis of Monofluoro Aryl Acetates via Decarboxylative Cross-Coupling

We report the Cu-promoted oxidative cross-coupling of -fluoromalonate half-esters and aryl boron reagents to deliver monofluoro -aryl acetates under mild conditions (in air at room temperature). The reaction uses a simple, readily available monofluorinated building block to generate arylated compoun...

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Bibliographic Details
Published inSynlett Vol. 28; no. 20; pp. 2886 - 2890
Main Authors Fahandej-Sadi, Anis, Lundgren, Rylan J.
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 18.12.2017
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
MEDICINAL CHEMISTRY
ACID-DERIVATIVES
ESTERS
cross-coupling
copper
aerobic catalysis
ETHYL BROMOFLUOROACETATE
ALPHA-FLUORINATION
arylation
fluorine
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Summary:We report the Cu-promoted oxidative cross-coupling of -fluoromalonate half-esters and aryl boron reagents to deliver monofluoro -aryl acetates under mild conditions (in air at room temperature). The reaction uses a simple, readily available monofluorinated building block to generate arylated compounds with functional groups that are not easily tolerated by existing methods, such as aryl bromides, iodides, pyridines, and pyrimidines.
ISSN:0936-5214
1437-2096
DOI:10.1055/s-0036-1588516