Palladium-Mediated Catalysis Leads to Intramolecular Narcissistic Self-Sorting on a Cavitand Platform

Autor(es)

Nagymihaly, Zoltan ; Caturello, Naidel A. M. S. ; Takatsy, Aniko ; Aragay, Gemma ; Kollar, Laszlo ; Albuquerque, Rodrigo Q. ; Csok, Zsolt

• Tipo de documento: Artigo Científico
• Fonte: Journal of Organic Chemistry; v. 82, n. 1, p. 390-396, JAN 6 2017.
• Citações Web of Science: 2

Resumo

Palladium-catalyzed aminocarbonylation reactions have been used to directly convert a tetraiodocavitand intermediate into the corresponding carboxamides and 2-ketocarboxamides. When complex mixtures of the amine reactants are employed in competition experiments using polar solvents, such as DMF, no ``mixed{''} products possessing structurally different amide fragments are detected either by H-1 or C-13 NMR Only highly symmetrical cavitands are sorted out of a large number of potentially feasible products, which represents a rare example of intramolecular, narcissistic self-sorting. Our experimental results along with thermodynamic energy analysis suggest that the observed self-sorting is a symmetry-driven, kinetically controlled process. (AU)

• Processo FAPESP: 14/02071-5 - Investigação teórica da agregação de complexos catiônicos de Ir(III) com potencial aplicação em LECs e OLEDs
• Beneficiário: Rodrigo Queiroz de Albuquerque
• Modalidade de apoio: Auxílio à Pesquisa - Regular