Issue 30, 2016

Late stage trifluoromethylthiolation strategies for organic compounds

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

Article information

Article type
Review Article
Submitted
10 Apr 2016
Accepted
08 Jun 2016
First published
08 Jun 2016

Org. Biomol. Chem., 2016,14, 7150-7182

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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