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Issue 30, 2016
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Late stage trifluoromethylthiolation strategies for organic compounds

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Abstract

Substitution by the CF3S group allows for an increase in lipophilicity and electron-withdrawing properties along with an improvement in the bioavailability of medicinal targets; consequently, the late stage introduction of CF3S moieties into medicinal scaffolds is a sought-after strategy in synthetic organic chemistry. 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.

Graphical abstract: Late stage trifluoromethylthiolation strategies for organic compounds

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Publication details

The article was received on 10 Apr 2016, accepted on 08 Jun 2016 and first published on 08 Jun 2016


Article type: Review Article
DOI: 10.1039/C6OB00763E
Citation: Org. Biomol. Chem., 2016,14, 7150-7182
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    Late stage trifluoromethylthiolation strategies for organic compounds

    S. Barata-Vallejo, S. Bonesi and A. Postigo, Org. Biomol. Chem., 2016, 14, 7150
    DOI: 10.1039/C6OB00763E

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