Late stage trifluoromethylthiolation strategies for organic compounds

BARATA VALLEJO, SEBASTIAN; BONESI SERGIO M; POSTIGO J. ALBERTO

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 liphophilicity and electron-withdrawing properties along with an improvement in the bioavailability of medicinal targets. Methods to accomplish such substitutions can be nucleophilic and electrophilic in nature. Different newly-developed electrophilic and nucleophilic reagents are used to effect the trifluoromethylthiolation of (hetero)aromatic compounds, aliphatic compounds (alkyl, alkenyl, alkynyl substrates), the trifluoromethylthiolation 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 ring-cyclizations will be shown to yield relevant CF3S-substituted heteroaromatic compounds with relevant pharmacological action.