Direct Nucleophilic Difluoromethylation of Carbonyl Compounds

Phosphonium salt ([Ph3P+CF2H] Br–, DFPB) was found to be an efficient nucleophilic difluoromethylation reagent. Although DFPB is known as a phosphonium ylide precursor, its reaction with carbonyl compounds under traditional “Wittig reaction conditions” did not give the expected Wittig difluoroolefin...

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Bibliographic Details
Published inOrganic letters Vol. 18; no. 13; pp. 3206 - 3209
Main Authors Deng, Zuyong, Lin, Jin-Hong, Cai, Ji, Xiao, Ji-Chang
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 01.07.2016
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
REAGENT
IODIDES
QUATERNARY PHOSPHONIUM HYDROXIDES
WITTIG REACTION
GEM-DIFLUOROOLEFINATION
COPPER-MEDIATED DIFLUOROMETHYLATION
DECOMPOSITION
ALDEHYDES
SUBSTITUTION-REACTIONS
SALTS
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Summary:Phosphonium salt ([Ph3P+CF2H] Br–, DFPB) was found to be an efficient nucleophilic difluoromethylation reagent. Although DFPB is known as a phosphonium ylide precursor, its reaction with carbonyl compounds under traditional “Wittig reaction conditions” did not give the expected Wittig difluoroolefinated products, but afforded the nucleophilic difluoromethylation products, α-CF2H alcohols. Mechanistic investigation reveals that the unexpected transformation proceeded via the direct transfer of the CF2H group, which resulted from the high P–O affinity.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.6b01425