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Photoredox-Catalyzed α-C-H Monoalkylation of Symmetric Polyols in the Presence of CO2.
Archer, Gaétan; Meyrelles, Ricardo; Eder, Isabel; Kovács, Nóra; Maryasin, Boris; Médebielle, Maurice; Merad, Jérémy.
Afiliación
  • Archer G; ICBMS, UMR 5246, Univ Lyon, Université Lyon 1, CNRS, INSA, CPE-Lyon, ICBMS, 1 rue Victor Grignard, 69622, Villeurbanne, France.
  • Meyrelles R; Institute of Theoretical Chemistry, University of Vienna, Währinger Straße 17, 1090, Vienna, Austria.
  • Eder I; Institute of Organic Chemistry, University of Vienna, Währinger Straße 38, 1090, Vienna, Austria.
  • Kovács N; Vienna Doctoral School in Chemistry, University of Vienna, Währinger Straße 42, 1090, Vienna, Austria.
  • Maryasin B; Institute of Theoretical Chemistry, University of Vienna, Währinger Straße 17, 1090, Vienna, Austria.
  • Médebielle M; Institute of Theoretical Chemistry, University of Vienna, Währinger Straße 17, 1090, Vienna, Austria.
  • Merad J; Institute of Theoretical Chemistry, University of Vienna, Währinger Straße 17, 1090, Vienna, Austria.
Angew Chem Int Ed Engl ; 63(6): e202315329, 2024 Feb 05.
Article en En | MEDLINE | ID: mdl-38091251
Achieving the selective modification of symmetric poly-hydroxylated compounds presents a significant challenge due to the presence of identical active sites. Herein, we address this challenge through the design of a ternary catalytic system that includes a photoredox catalyst, a hydrogen atom transfer promotor and a carbonation catalyst. This catalytic system enables the reversible carbonation of acyclic polyols under CO2 atmosphere, which modulates the reactivity of its distinct C-H bonds toward hydrogen atom transfers. An exquisite selectivity for the monoalkylation is achieved in a variety of unprotected light polyols, yielding valuable building blocks in short reaction times. Mechanistic and computational studies demonstrate that the formation of an intramolecular hydrogen bond between the transient carbonate and the free alcohol is pivotal for the kinetic and thermodynamic activation of a specific alcohol.
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Idioma: En Revista: Angew Chem Int Ed Engl Año: 2024 Tipo del documento: Article País de afiliación: Francia Pais de publicación: Alemania
Texto completo
Añadir a Mi BVS
Imprimir
XML
PubMed Links
Buscar en Google

Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Idioma: En Revista: Angew Chem Int Ed Engl Año: 2024 Tipo del documento: Article País de afiliación: Francia Pais de publicación: Alemania