LATE STAGE TRIFLUOROMETHYLTHIOLATION STRATEGIES FOR ORGANIC COMPOUNDS

SEBASTIAN BARATA VALLEJO; AL POSTIGO; SERGIO BONESI

ORGANIC & BIOMOLECULAR CHEMISTRY

ROYAL SOC CHEMISTRY

Lugar: CAMBRIDGE; Año: 2016 vol. 14 p. 7150 - 7182

1477-0520

Substitution by the CF3S group allows for an increase in lipophilicity and electronwithdrawingproperties along with an improvement in the bioavailability of medicinaltargets; consequently, the late stage introduction of CF3S moieties into medicinal scaffoldsis a sought-after strategy in synthetic organic chemistry. Different newly-developedelectrophilic and nucleophilic reagents are used to effect the trifluoromethylthiolation of(hetero)aromatic compounds, aliphatic compounds (alkyl, alkenyl, alkynyl substrates), thetrifluoromethylthiolation at the α- and β-carbonyl positions, and heteroatoms (N- and S-).Such reactions can involve homolytic substitutions, or functional-group substitutions (ipso).Addition reactions of electrophilic reagents to double and triple bonds followed by ringcyclizationswill be shown to yield relevant CF3S-substituted heteroaromatic compoundswith relevant pharmacological action.