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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. © 2016 The Royal Society of Chemistry.

Registro:

Documento: Artículo
Título:Late stage trifluoromethylthiolation strategies for organic compounds
Autor:Barata-Vallejo, S.; Bonesi, S.; Postigo, A.
Filiación:Departamento de Química Orgánica, Facultad de Farmacia y Bioquímica, Universidad de Buenos Aires, CONICET, Junín 954, Buenos Aires, CP 1113, Argentina
Departamento de Química Orgánica, CIHIDECAR-CONICET, Ciudad Universitaria, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Pabellón II, 3er piso, Buenos Aires, 1428, Argentina
Palabras clave:Addition reactions; Biochemistry; Chemical bonds; Scaffolds; Aliphatic compound; Electronwithdrawing; Electrophilic reagents; Heteroaromatic compounds; Homolytic substitution; Lipophilicity; Nucleophilic reagent; Synthetic organic chemistry; Carbonyl compounds
Año:2016
Volumen:14
Número:30
Página de inicio:7150
Página de fin:7182
DOI: http://dx.doi.org/10.1039/c6ob00763e
Título revista:Organic and Biomolecular Chemistry
Título revista abreviado:Org. Biomol. Chem.
ISSN:14770520
CODEN:OBCRA
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_14770520_v14_n30_p7150_BarataVallejo

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Citas:

---------- APA ----------
Barata-Vallejo, S., Bonesi, S. & Postigo, A. (2016) . Late stage trifluoromethylthiolation strategies for organic compounds. Organic and Biomolecular Chemistry, 14(30), 7150-7182.
http://dx.doi.org/10.1039/c6ob00763e
---------- CHICAGO ----------
Barata-Vallejo, S., Bonesi, S., Postigo, A. "Late stage trifluoromethylthiolation strategies for organic compounds" . Organic and Biomolecular Chemistry 14, no. 30 (2016) : 7150-7182.
http://dx.doi.org/10.1039/c6ob00763e
---------- MLA ----------
Barata-Vallejo, S., Bonesi, S., Postigo, A. "Late stage trifluoromethylthiolation strategies for organic compounds" . Organic and Biomolecular Chemistry, vol. 14, no. 30, 2016, pp. 7150-7182.
http://dx.doi.org/10.1039/c6ob00763e
---------- VANCOUVER ----------
Barata-Vallejo, S., Bonesi, S., Postigo, A. Late stage trifluoromethylthiolation strategies for organic compounds. Org. Biomol. Chem. 2016;14(30):7150-7182.
http://dx.doi.org/10.1039/c6ob00763e