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Photoinduced Halogen-Atom Transfer by N-Heterocyclic Carbene-Ligated Boryl Radicals for C(sp3)-C(sp3) Bond Formation.
Wan, Ting; Capaldo, Luca; Ravelli, Davide; Vitullo, Walter; de Zwart, Felix J; de Bruin, Bas; Noël, Timothy.
Afiliación
  • Wan T; Flow Chemistry Group, van 't Hoff Institute for Molecular Sciences (HIMS), University of Amsterdam, Science Park 904, 1098 XH Amsterdam, The Netherlands.
  • Capaldo L; Flow Chemistry Group, van 't Hoff Institute for Molecular Sciences (HIMS), University of Amsterdam, Science Park 904, 1098 XH Amsterdam, The Netherlands.
  • Ravelli D; PhotoGreen Lab, Department of Chemistry, University of Pavia, viale Taramelli 12, 27100 Pavia, Italy.
  • Vitullo W; Flow Chemistry Group, van 't Hoff Institute for Molecular Sciences (HIMS), University of Amsterdam, Science Park 904, 1098 XH Amsterdam, The Netherlands.
  • de Zwart FJ; Homogeneous, Supramolecular and Bio-inspired Catalysis Group (HomKat), van't Hoff Institute for Molecular Sciences (HIMS), Universiteit van Amsterdam (UvA), Science Park 904, 1098 XH, Amsterdam, The Netherlands.
  • de Bruin B; Homogeneous, Supramolecular and Bio-inspired Catalysis Group (HomKat), van't Hoff Institute for Molecular Sciences (HIMS), Universiteit van Amsterdam (UvA), Science Park 904, 1098 XH, Amsterdam, The Netherlands.
  • Noël T; Flow Chemistry Group, van 't Hoff Institute for Molecular Sciences (HIMS), University of Amsterdam, Science Park 904, 1098 XH Amsterdam, The Netherlands.
J Am Chem Soc ; 145(2): 991-999, 2023 01 18.
Article en En | MEDLINE | ID: mdl-36583709
Herein, we present a comprehensive study on the use of N-heterocyclic carbene (NHC)-ligated boryl radicals to enable C(sp3)-C(sp3) bond formation under visible-light irradiation via Halogen-Atom Transfer (XAT). The methodology relies on the use of an acridinium dye to generate the boron-centered radicals from the corresponding NHC-ligated boranes via single-electron transfer (SET) and deprotonation. These boryl radicals subsequently engage with alkyl halides in an XAT step, delivering the desired nucleophilic alkyl radicals. The present XAT strategy is very mild and accommodates a broad scope of alkyl halides, including medicinally relevant compounds and biologically active molecules. The key role of NHC-ligated boryl radicals in the operative reaction mechanism has been elucidated through a combination of experimental, spectroscopic, and computational studies. This methodology stands as a significant advancement in the chemistry of NHC-ligated boryl radicals, which had long been restricted to radical reductions, enabling C-C bond formation under visible-light photoredox conditions.
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Halógenos / Metano Idioma: En Revista: J Am Chem Soc Año: 2023 Tipo del documento: Article País de afiliación: Países Bajos Pais de publicación: Estados Unidos
Texto completo
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Halógenos / Metano Idioma: En Revista: J Am Chem Soc Año: 2023 Tipo del documento: Article País de afiliación: Países Bajos Pais de publicación: Estados Unidos