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Organocatalyzed Carbonylation of Alkyl Halides Driven by Visible Light.
Liu, Xin; Portela, Brandon S; Wiedenbeck, Analiese; Chrisman, Cameron H; Paton, Robert S; Miyake, Garret M.
Afiliación
  • Liu X; Department of Chemistry, Colorado State University, Center Ave, Fort Collins, CO 80523, United States.
  • Portela BS; Department of Chemistry, Colorado State University, Center Ave, Fort Collins, CO 80523, United States.
  • Wiedenbeck A; Department of Chemistry, Colorado State University, Center Ave, Fort Collins, CO 80523, United States.
  • Chrisman CH; Department of Chemistry, Colorado State University, Center Ave, Fort Collins, CO 80523, United States.
  • Paton RS; Department of Chemistry, Colorado State University, Center Ave, Fort Collins, CO 80523, United States.
  • Miyake GM; Department of Chemistry, Colorado State University, Center Ave, Fort Collins, CO 80523, United States.
Angew Chem Int Ed Engl ; : e202410928, 2024 Aug 07.
Article en En | MEDLINE | ID: mdl-39110753
ABSTRACT
Herein, we describe a new strategy for the carbonylation of alkyl halides with different nucleophiles to generate valuable carbonyl derivatives under visible light irradiation. This method is mild, robust, highly selective, and proceeds under metal-free conditions to prepare a range of structurally diverse esters and amides in good to excellent yields. In addition, we highlight the application of this activation strategy for 13C isotopic incorporation. We propose that the reaction proceeds by a photoinduced reduction to afford carbon-centered radicals from alkyl halides, which undergo subsequent single electron-oxidation to form a carbocationic intermediate. Carbon monoxide is trapped by the carbocation to generate an acylium cation, which can be attacked by a series of nucleophiles to give a range of carbonyl products.
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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: Estados Unidos 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: Estados Unidos Pais de publicación: Alemania