Synthesis of monofluoroalkenes via Julia–Kocienski reaction

Monofluoromethyl 3,5-bis(trifluoromethyl)phenyl sulfone 1 was synthesized and employed in Julia–Kocienski fluoroolefination reaction with various ketones and aldehydes. Optimal reaction conditions were found to be the treatment of substrates with KOH or CsF in DMSO at room temperature. Mixtures of (...

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Published inJournal of fluorine chemistry Vol. 131; no. 11; pp. 1192 - 1197
Main Authors Prakash, G.K. Surya, Shakhmin, Anton, Zibinsky, Mikhail, Ledneczki, Istvan, Chacko, Sujith, Olah, George A.
Format Journal Article
LanguageEnglish
Published LAUSANNE Elsevier B.V 01.11.2010
Elsevier
Subjects
Aldehydes
Chemistry
Chemistry, Inorganic & Nuclear
Chemistry, Organic
Fluorine
Isomers
Julia–Kocienski reaction
Ketones
Monofluoroalkenes
Monofluoromethyl arylsulfone
Monofluoroolefination
Optimization
Physical Sciences
Science & Technology
Sulfones
Synthesis (chemistry)
Monofluoromethyl arylsulfone
Monofluoroolefination
Monofluoroalkenes
Julia–Kocienski reaction
ALCOHOLS
ROUTE
EFFICIENT
FLUORIDES
Julia-Kocienski reaction
AMIDES
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Summary:Monofluoromethyl 3,5-bis(trifluoromethyl)phenyl sulfone 1 was synthesized and employed in Julia–Kocienski fluoroolefination reaction with various ketones and aldehydes. Optimal reaction conditions were found to be the treatment of substrates with KOH or CsF in DMSO at room temperature. Mixtures of ( E) and ( Z) isomers of monofluoroalkenes 4 were obtained in moderate to excellent yields. [Display omitted]
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0022-1139
1873-3328
DOI:10.1016/j.jfluchem.2010.06.009