Copper-Catalyzed Decarboxylative Trifluoromethylation of Allylic Bromodifluoroacetates

The development of new synthetic fluorination reactions has important implications in medicinal, agricultural, and materials chemistries. Given the prevalence and accessibility of alcohols, methods to convert alcohols to trifluoromethanes are desirable. However, this transformation typically require...

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Bibliographic Details
Published inOrganic letters Vol. 15; no. 21; pp. 5578 - 5581
Main Authors Ambler, Brett R, Altman, Ryan A
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 01.11.2013
Amer Chemical Soc
Subjects
Acetates - chemistry
Catalysis
Chemistry
Chemistry, Organic
Copper - chemistry
Hydrocarbons, Fluorinated - chemistry
Methylation
Molecular Structure
Physical Sciences
Propanols - chemistry
Science & Technology
Stereoisomerism
NUCLEOPHILIC TRIFLUOROMETHYLATION
CHLORODIFLUOROACETATE
ACID
ANALOGS
DIFLUOROCARBENE PRECURSORS
ARYL HALIDES
ORGANIC HALIDES
GENERATION
FLUORINATION
DERIVATIVES
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Summary:The development of new synthetic fluorination reactions has important implications in medicinal, agricultural, and materials chemistries. Given the prevalence and accessibility of alcohols, methods to convert alcohols to trifluoromethanes are desirable. However, this transformation typically requires four-step processes, specialty chemicals, and/or stoichiometric metals to access the trifluoromethyl-containing product. A two-step copper-catalyzed decarboxylative protocol for converting allylic alcohols to trifluoromethanes is reported. Preliminary mechanistic studies distinguish this reaction from previously reported Cu-mediated reactions.
Bibliography:NIH RePORTER
ObjectType-Article-1
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ISSN:1523-7060
1523-7052
DOI:10.1021/ol402780k