Synthesis of CF3-Substituted Sulfoximines from Sulfonimidoyl Fluorides

N-Protected trifluoromethyl-substituted sulfoximines have been prepared by treatment of sulfonimidoyl fluorides with a combination of the Ruppert−Prakash reagent (TMSCF3) and tetrabutyl ammonium fluoride (TBAF). The starting materials were accessed following two synthetic routes, and for each reacti...

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Published inOrganic letters Vol. 13; no. 4; pp. 768 - 771
Main Authors Kowalczyk, Rafal, Edmunds, Andrew J. F, Hall, Roger G, Bolm, Carsten
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 18.02.2011
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
SULFOXIDES
REAGENTS
RHODIUM
EFFICIENT PREPARATION
SULFILIMINES
ORGANOFLUORINE CHEMISTRY
SULFINYL CHLORIDES
CATALYZED IMINATION
PERFLUOROALKYLATION
TRIFLUOROMETHYLATION
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Summary:N-Protected trifluoromethyl-substituted sulfoximines have been prepared by treatment of sulfonimidoyl fluorides with a combination of the Ruppert−Prakash reagent (TMSCF3) and tetrabutyl ammonium fluoride (TBAF). The starting materials were accessed following two synthetic routes, and for each reaction sequence the substrate scope was evaluated. Accordingly, a wide variety of aryl-substituted products were obtained in moderate to good yield.
Bibliography:ObjectType-Article-1
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ISSN:1523-7060
1523-7052
DOI:10.1021/ol103030w