Deoxygenative gem-difluorovinylation of aliphatic alcohols

An unprecedented deoxygenative gem-difluorovinylation of aliphatic alcohols using alpha-trifluoromethyl alkenes is achieved under photocatalytic conditions. Inexpensive Ph3P acts as an efficient O-atom transfer reagent to facilitate the deoxygenation of alcohols for the generation of reactive alkyl...

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Published inChemical communications (Cambridge, England) Vol. 58; no. 47; pp. 6733 - 6736
Main Authors Xia, Guang-Da, He, Yuan-Yuan, Zhang, Jing, Liu, Zi-Kui, Gao, Yang, Hu, Xiao-Qiang
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 09.06.2022
Royal Society of Chemistry
Subjects
Aliphatic alcohols
Alkenes
Chemical synthesis
Chemistry
Chemistry, Multidisciplinary
Deoxygenation
Diols
Physical Sciences
Reagents
Science & Technology
MITSUNOBU
HYDROAMINATION
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Summary:An unprecedented deoxygenative gem-difluorovinylation of aliphatic alcohols using alpha-trifluoromethyl alkenes is achieved under photocatalytic conditions. Inexpensive Ph3P acts as an efficient O-atom transfer reagent to facilitate the deoxygenation of alcohols for the generation of reactive alkyl radical species. Remarkable features of this reaction include mild conditions, simple operation and broad scope. The synthetic utility of this reaction was validated by the success of two-step one-pot reactions, scale-up synthesis and chemoselective monodeoxygenation of diols.
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ISSN:1359-7345
1364-548X
DOI:10.1039/d2cc01918c