Electrochemical trifluoromethylation/semipinacol rearrangement sequences of alkenyl alcohols: synthesis of beta-CF3-substituted ketones

Electrochemical oxidative radical trifluoromethylation/ semipinacol rearrangement sequences of alkenyl alcohols were developed in this study. This approach is environmentally benign and uses the shelf-stable Langlois reagent as a trifluoromethyl radical precursor and electrons as the oxidizing reage...

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Bibliographic Details
Published inOrganic & biomolecular chemistry Vol. 17; no. 13; pp. 3319 - 3323
Main Authors Jung, Hye Im, Kim, Yubin, Kim, Dae Young
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 07.04.2019
Royal Society of Chemistry
Subjects
Alcohol
Alcohols
Chemistry
Chemistry, Organic
Electrochemistry
Ketones
Organic chemistry
Oxidation
Physical Sciences
Reagents
Science & Technology
DIFUNCTIONALIZATION
FUNCTIONALIZATION
ASYMMETRIC-SYNTHESIS
RING EXPANSION
VISIBLE-LIGHT PHOTOREDOX
CONSTRUCTION
SEMIPINACOL REARRANGEMENT
FLUORINE
MIGRATION SEQUENCES
C-H TRIFLUOROMETHYLATION
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Summary:Electrochemical oxidative radical trifluoromethylation/ semipinacol rearrangement sequences of alkenyl alcohols were developed in this study. This approach is environmentally benign and uses the shelf-stable Langlois reagent as a trifluoromethyl radical precursor and electrons as the oxidizing reagents. The present protocol offers a facile route to prepare beta-trifluoromethylated ketone derivatives.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
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ISSN:1477-0520
1477-0539
DOI:10.1039/c9ob00373h