Trifluoromethylthiolation of Arenes Using Lewis Acid and Lewis Base Dual Catalysis

Incorporation of the highly lipophilic trifluoromethanesulfenyl group into bioactive molecules facilitates transport through lipid membranes, and thus, CF3S-containing compounds are important for drug discovery. Although reagents and procedures have been reported for arene trifluoromethylthiolation,...

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Bibliographic Details
Published inJournal of organic chemistry Vol. 89; no. 2; pp. 1275 - 1284
Main Authors Waddell, Lachlan J. N., Wilson, Claire, Sutherland, Andrew
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 19.01.2024
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
HYPERVALENT IODINE REAGENT
REACTIVITY
ETHERS
DERIVATIVES
THIOETHERS
ELECTROPHILIC TRIFLUOROMETHYLTHIOLATION
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Summary:Incorporation of the highly lipophilic trifluoromethanesulfenyl group into bioactive molecules facilitates transport through lipid membranes, and thus, CF3S-containing compounds are important for drug discovery. Although reagents and procedures have been reported for arene trifluoromethylthiolation, methods are still required that are applicable to a diverse substrate scope and can be performed under mild conditions. Here, we describe a rapid and efficient approach for the trifluoromethylthiolation of arenes by catalytic activation of N-trifluoromethylthiosaccharin using a combination of iron­(III) chloride and diphenyl selenide. This dual catalytic process allowed regioselective functionalization of a wide range of arenes and N-heterocycles under mild conditions and was used for the trifluoromethylthiolation of bioactive compounds such as tyrosine and estradiol.
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ISSN:0022-3263
1520-6904
1520-6904
DOI:10.1021/acs.joc.3c02571