Late stage trifluoromethylthiolation strategies for organic compounds
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 syntheti...
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| Acceso en línea: | http://hdl.handle.net/20.500.12110/paper_14770520_v14_n30_p7150_BarataVallejo |
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todo:paper_14770520_v14_n30_p7150_BarataVallejo2023-10-03T16:19:04Z Late stage trifluoromethylthiolation strategies for organic compounds Barata-Vallejo, S. Bonesi, S. Postigo, A. Addition reactions Biochemistry Chemical bonds Scaffolds Aliphatic compound Electronwithdrawing Electrophilic reagents Heteroaromatic compounds Homolytic substitution Lipophilicity Nucleophilic reagent Synthetic organic chemistry Carbonyl compounds 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. Fil:Bonesi, S. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. JOUR info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar http://hdl.handle.net/20.500.12110/paper_14770520_v14_n30_p7150_BarataVallejo |
| institution |
Universidad de Buenos Aires |
| institution_str |
I-28 |
| repository_str |
R-134 |
| collection |
Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) |
| topic |
Addition reactions Biochemistry Chemical bonds Scaffolds Aliphatic compound Electronwithdrawing Electrophilic reagents Heteroaromatic compounds Homolytic substitution Lipophilicity Nucleophilic reagent Synthetic organic chemistry Carbonyl compounds |
| spellingShingle |
Addition reactions Biochemistry Chemical bonds Scaffolds Aliphatic compound Electronwithdrawing Electrophilic reagents Heteroaromatic compounds Homolytic substitution Lipophilicity Nucleophilic reagent Synthetic organic chemistry Carbonyl compounds Barata-Vallejo, S. Bonesi, S. Postigo, A. Late stage trifluoromethylthiolation strategies for organic compounds |
| topic_facet |
Addition reactions Biochemistry Chemical bonds Scaffolds Aliphatic compound Electronwithdrawing Electrophilic reagents Heteroaromatic compounds Homolytic substitution Lipophilicity Nucleophilic reagent Synthetic organic chemistry Carbonyl compounds |
| description |
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. |
| format |
JOUR |
| author |
Barata-Vallejo, S. Bonesi, S. Postigo, A. |
| author_facet |
Barata-Vallejo, S. Bonesi, S. Postigo, A. |
| author_sort |
Barata-Vallejo, S. |
| title |
Late stage trifluoromethylthiolation strategies for organic compounds |
| title_short |
Late stage trifluoromethylthiolation strategies for organic compounds |
| title_full |
Late stage trifluoromethylthiolation strategies for organic compounds |
| title_fullStr |
Late stage trifluoromethylthiolation strategies for organic compounds |
| title_full_unstemmed |
Late stage trifluoromethylthiolation strategies for organic compounds |
| title_sort |
late stage trifluoromethylthiolation strategies for organic compounds |
| url |
http://hdl.handle.net/20.500.12110/paper_14770520_v14_n30_p7150_BarataVallejo |
| work_keys_str_mv |
AT baratavallejos latestagetrifluoromethylthiolationstrategiesfororganiccompounds AT bonesis latestagetrifluoromethylthiolationstrategiesfororganiccompounds AT postigoa latestagetrifluoromethylthiolationstrategiesfororganiccompounds |
| _version_ |
1807316090749976576 |