Your browser doesn't support javascript.
loading
Mechanistic studies of copper(I)-catalyzed 1,3-halogen migration.
Van Hoveln, Ryan; Hudson, Brandi M; Wedler, Henry B; Bates, Desiree M; Le Gros, Gabriel; Tantillo, Dean J; Schomaker, Jennifer M.
Afiliación
  • Van Hoveln R; †Department of Chemistry, University of Wisconsin, Madison, Wisconsin 53706, United States.
  • Hudson BM; ‡Department of Chemistry, University of California, Davis, California 95616, United States.
  • Wedler HB; ‡Department of Chemistry, University of California, Davis, California 95616, United States.
  • Bates DM; †Department of Chemistry, University of Wisconsin, Madison, Wisconsin 53706, United States.
  • Le Gros G; †Department of Chemistry, University of Wisconsin, Madison, Wisconsin 53706, United States.
  • Tantillo DJ; ‡Department of Chemistry, University of California, Davis, California 95616, United States.
  • Schomaker JM; †Department of Chemistry, University of Wisconsin, Madison, Wisconsin 53706, United States.
J Am Chem Soc ; 137(16): 5346-54, 2015 Apr 29.
Article en En | MEDLINE | ID: mdl-25828031
ABSTRACT
An ongoing challenge in modern catalysis is to identify and understand new modes of reactivity promoted by earth-abundant and inexpensive first-row transition metals. Herein, we report a mechanistic study of an unusual copper(I)-catalyzed 1,3-migration of 2-bromostyrenes that reincorporates the bromine activating group into the final product with concomitant borylation of the aryl halide bond. A combination of experimental and computational studies indicated this reaction does not involve any oxidation state changes at copper; rather, migration occurs through a series of formal sigmatropic shifts. Insight provided from these studies will be used to expand the utility of aryl copper species in synthesis and develop new ligands for enantioselective copper-catalyzed halogenation.
Asunto(s)
Texto completo
Imprimir
XML
PubMed Links
Buscar en Google

Texto completo: 1 Colección: 01-internacional Banco de datos: MEDLINE Asunto principal: Estirenos / Bromo / Cobre Idioma: En Revista: J Am Chem Soc Año: 2015 Tipo del documento: Article País de afiliación: Estados Unidos
Texto completo
Imprimir
XML
PubMed Links
Buscar en Google

Texto completo: 1 Colección: 01-internacional Banco de datos: MEDLINE Asunto principal: Estirenos / Bromo / Cobre Idioma: En Revista: J Am Chem Soc Año: 2015 Tipo del documento: Article País de afiliación: Estados Unidos