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Deoxytrifluoromethylation/aromatization of cyclohexan(en)ones to access highly substituted trifluoromethyl arenes.
Bhattarai, Pankaj; Abd El-Gaber, Mohammed K; Koley, Suvajit; Altman, Ryan A.
Afiliación
  • Bhattarai P; Borch Department of Medicinal Chemistry and Molecular Pharmacology, Purdue University, West Lafayette, IN, 47907, USA.
  • Abd El-Gaber MK; Borch Department of Medicinal Chemistry and Molecular Pharmacology, Purdue University, West Lafayette, IN, 47907, USA.
  • Koley S; Medicinal Chemistry Department, Assiut University; Assiut, 71526, Egypt & Department of Pharmaceutical Sciences, University of Tennessee Health Science Center, Memphis, TN, 38163, USA.
  • Altman RA; Borch Department of Medicinal Chemistry and Molecular Pharmacology, Purdue University, West Lafayette, IN, 47907, USA.
Nat Commun ; 15(1): 7882, 2024 Sep 09.
Article en En | MEDLINE | ID: mdl-39251584
ABSTRACT
Trifluoromethyl arenes (Ar-CF3) are amongst the commonly encountered fluorinated substructures in pharmaceutical, agrochemical, and material sciences. However, predominant methods to access Ar-CF3 possess several limitations, including harsh conditions, lack of availability of substrates, and poor regioselectivity, which combined restrict access to desirable highly functionalized Ar-CF3-containing compounds. To expand the scope of accessible Ar-CF3-based molecules, we present an orthogonal deoxyfluoroalkylation/aromatization approach that exploits readily accessible and programable cyclohexan(en)one substrates, which undergo a reliable 1,2-addition reaction with the Ruppert-Prakash reagent (TMSCF3) followed by aromatization to deliver highly functionalized Ar-CF3 compounds in a one/two-pot sequence. This general strategy enables access to highly substituted Ar-CF3-containing molecules that are difficult, expensive, and/or impossible to access by current synthetic methods.
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Idioma: En Revista: Nat Commun Asunto de la revista: BIOLOGIA / CIENCIA Año: 2024 Tipo del documento: Article País de afiliación: Estados Unidos Pais de publicación: Reino Unido
Texto completo
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Imprimir
XML
PubMed Links
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Idioma: En Revista: Nat Commun Asunto de la revista: BIOLOGIA / CIENCIA Año: 2024 Tipo del documento: Article País de afiliación: Estados Unidos Pais de publicación: Reino Unido