Synthesis and Applications of Fluorinated Sulfoxides ( RSOR _F ) and Sulfones ( RSO ₂ R _F )

ortho-Cyanomethylation of aryl fluoroalkyl sulfoxides via a sulfonium–Claisen rearrangement

“…8,9 Furthermore, they could also serve as pivotal groups for accessing other highly appreciated derivatives, such as fluorinated sulfones, sulfonamides, and sulfoximines. 10 Therefore, the incorporation of both the cyanomethyl group and the fluoroalkylthio group into arenes is a useful endeavor.…”

Straightforward Synthesis of Bis[(trifluoromethyl)sulfonyl]ethylated Isocoumarins from 2-Ethynylbenzoates

“…On the other hand, the SO 2 CF 3 (Tf, triflyl) group is an appealing moiety because it combines the presence of two prominent functionalities, namely, the sulfone motif and the organofluorinated structure. The appearance of the strongly electron-withdrawing Tf moiety in drugs provides an improvement in the metabolic stability and lipophilicity . In addition, the enhancement of both water solubility in bioactive molecules and dyes and catalytic activity in organocatalysts by the presence of the Tf 2 CH substituent has been documented .…”

“…The appearance of the strongly electron-withdrawing Tf moiety in drugs provides an improvement in the metabolic stability and lipophilicity. 7 In addition, the enhancement of both water solubility in bioactive molecules and dyes and catalytic activity in organocatalysts by the presence of the Tf 2 CH substituent has been documented. 8 Although the incorporation of the bis(triflyl)alkyl group is challenging, Yanai et al pioneered the use of shelf-stable and readily available betaine 1 as source of Tf 2 C=CH 2 .…”

Organocatalytic Synthesis of Triflones Bearing Two Non‐Adjacent Stereogenic Centers

“…Whereas several methods for the synthesis of achiral or racemic triflones are available, stereoselective methods that provide C α -disubstituted triflones are scarce despite their synthetic utility. [9,10] The few reported examples rely on the enantioselective reaction of α-triflyl carbanions with electrophiles, [7,11] or the oxidation of chiral SCF 3 -containing compounds (Scheme 1A, left). [7,12] An alternative, concep-tually different approach would be a stereoselective-ideally catalytic-conjugate addition reaction to α-substituted vinyl triflones (Scheme 1A, right).…”