Synthetic and Mechanistic Studies on the Solvent-Dependent Copper-Catalyzed Formation of Indolizines and Chalcones

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Title: Synthetic and Mechanistic Studies on the Solvent-Dependent Copper-Catalyzed Formation of Indolizines and Chalcones
Authors: Albaladejo Maricó, María José | Alonso, Francisco | González Soria, María José
Research Group/s: Nuevos Materiales y Catalizadores (MATCAT)
Center, Department or Service: Universidad de Alicante. Departamento de Química Orgánica | Universidad de Alicante. Instituto Universitario de Síntesis Orgánica
Keywords: Chalcones | Copper nanoparticles | Indolizines | Multicomponent reactions | Nitrogen heterocycles | Propargylamines | Reaction mechanisms
Knowledge Area: Química Orgánica
Issue Date: 27-Apr-2015
Publisher: American Chemical Society
Citation: ACS Catalysis. 2015, 5: 3446-3456. doi:10.1021/acscatal.5b00417
Abstract: Copper nanoparticles supported on activated carbon have been found to catalyze the multicomponent synthesis of indolizines from pyridine-2-carbaldehyde derivatives, secondary amines, and terminal alkynes in dichloromethane; in the absence of solvent, however, heterocyclic chalcones are formed. We provide compelling evidence that both processes take place through aldehyde–amine–alkyne coupling intermediates. In contrast to other well-known mechanisms for chalcone formation from aldehydes and alkynes, a new reaction pathway involving propargyl amines as intermediates that do not undergo rearrangement is presented. The formation of indolizines or chalcones is driven by inductive and solvent effects, with a wide array of both being reported. In both reactions, the nanoparticulate catalyst has been shown to be superior to some commercially available copper catalysts, and it could be recycled in the case of the chalcone synthesis.
Sponsor: This work was generously supported by the Spanish Ministerio de Economía y Competitividad (MINECO; CTQ2011-24151). M.J.A. and M.J.G.-S. acknowledge the Instituto de Síntesis Orgánica (ISO) of the Universidad de Alicante for both grants.
URI: http://hdl.handle.net/10045/46792
ISSN: 2155-5435
DOI: 10.1021/acscatal.5b00417
Language: eng
Type: info:eu-repo/semantics/article
Rights: © 2015 American Chemical Society
Peer Review: si
Publisher version: http://dx.doi.org/10.1021/acscatal.5b00417
Appears in Collections:INV - MATCAT - Artículos de Revistas

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