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Metal-Free Directed Site-Selective Csp3 -H Borylation of Saturated Cyclic Amines.
Kumar Someswara Ashwathappa, Puneeth; Higashi, Takuya; Desrosiers, Vincent; Omaña, Alvaro A; Fontaine, Frédéric-Georges.
Afiliación
  • Kumar Someswara Ashwathappa P; Département de Chimie, Université Laval, 1045 Avenue de la Médecine, Québec, Québec G1 V 0 A6, Canada.
  • Higashi T; Department of Chemistry and Biotechnology, Graduate School of Engineering, The University of Tokyo, Bunkyo-Ku, Tokyo 113-8656, Japan.
  • Desrosiers V; Département de Chimie, Université Laval, 1045 Avenue de la Médecine, Québec, Québec G1 V 0 A6, Canada.
  • Omaña AA; Département de Chimie, Université Laval, 1045 Avenue de la Médecine, Québec, Québec G1 V 0 A6, Canada.
  • Fontaine FG; Département de Chimie, Université Laval, 1045 Avenue de la Médecine, Québec, Québec G1 V 0 A6, Canada.
Angew Chem Int Ed Engl ; 62(39): e202309295, 2023 Sep 25.
Article en En | MEDLINE | ID: mdl-37535392
The borylation of Csp3 -H bonds is a challenging transformation that is typically restricted to transition metal catalysis. Herein, we report the site-selective metal-free Csp3 -H borylation of saturated cyclic amines. It is possible to selectively borylate piperidine derivatives at the α or ß positions according to the reaction conditions. The mechanism was supported by NMR spectroscopy, calorimetry experiments and density functional theory (DFT) computations. It suggests that the piperidine is dehydrogenated by complexation with BBr3 to produce an enamine intermediate, which is in turn borylated at either the α or ß position according to the reaction conditions.
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Idioma: En Revista: Angew Chem Int Ed Engl Año: 2023 Tipo del documento: Article País de afiliación: Canadá Pais de publicación: Alemania
Texto completo
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Idioma: En Revista: Angew Chem Int Ed Engl Año: 2023 Tipo del documento: Article País de afiliación: Canadá Pais de publicación: Alemania