One pot synthesis of trifluoromethyl aryl sulfoxides by trifluoromethylthiolation of arenes and subsequent oxidation with hydrogen peroxide

Abstract

Hydrogen peroxide was used for selective oxidation of various aryl trifluoromethyl sulfides.

AgSCF3 Radical Addition Based on an Oxidant-Free α,β-Amide (Trifluoromethyl)sulfanylation Reaction

“…Compared with (trifluoromethyl)sulfanylation reactions involving aromatic hydrocarbons 4a f , 9 10 11 12 13 or alkynes, 15 16 17 18 19 20 21 22 23 24 25 there are few reports on the (trifluoromethyl)sulfanylation reaction of olefins. 25 Many natural products and active drug molecules containing (trifluoromethyl)sulfanyl groups are obtained through the (trifluoromethyl)sulfanylation reaction of olefins.…”

Tuning CH Hydrogen Bond‐Based Receptors toward Picomolar Anion Affinity via the Inductive Effect of Distant Substituents

“…Bambusurils BU2 and BU3 were prepared by oxidation of glycoluril building block 1, followed by the macrocyclization reaction (Scheme 1). The oxidation of the −SCF 3 groups of 1 to sulphoxides was achieved in trifluoroacetic acid (TFA) using urea hydrogen peroxide adduct (UHP) as an oxidizing agent with a better defined hydrogen peroxide content than aqueous H 2 O 2 solutions [34] . Careful control of the amount of oxidizing agent and conducting the reaction at low temperature were necessary to avoid overoxidation to sulphone.…”

“…The oxidation of the À SCF 3 groups of 1 to sulphoxides was achieved in trifluoroacetic acid (TFA) using urea hydrogen peroxide adduct (UHP) as an oxidizing agent with a better defined hydrogen peroxide content than aqueous H 2 O 2 solutions. [34] Careful control of the amount of oxidizing agent and conducting the reaction at low temperature were necessary to avoid overoxidation to sulphone. The sulphone glycoluril derivative 3 was prepared by reacting 1 with an excess of m-CPBA at elevated temperature.…”

Oxidation of N-trifluoromethylthio sulfoximines using NaOCl·5H2O

“…The main challenge with oxidation to sulfoxides is the potential overoxidation to sulfones, which in some cases is as rapid as oxidation to sulfoxides. While the oxidation of non-halogenated sulfides is very well known and has through the years become increasingly green, 31 the oxidation of the trifluoromethylthio functional group is mostly achieved using halogenated media 32 or halogenated agents such as m -CPBA 33 or TCCA, 34 generating considerable amounts of harmful waste, or using metal catalysts. 35 To this end, we have used solid sodium hypochlorite pentahydrate (NaOCl·5H 2 O) as a benign and selective oxidant.…”