title: Palladium-Mediated Catalysis Leads to Intramolecular Narcissistic Self-Sorting on a Cavitand Platform.
abstract: 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 by1H or13C 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.
authors.affiliation: Department of Inorganic Chemistry and MTA-PTE Research Group for Selective Chemical Syntheses, University of Pécs , Ifjúság 6, 7624 Pécs, Hungary.
authors.forename: Zoltán
authors.initials: Z
authors.lastname: Nagymihály
authors.affiliation: São Carlos Institute of Chemistry, University of São Paulo , Av. Trab. São-carlense 400, 13560-970 São Carlos, SP, Brazil.
authors.forename: Naidel A M S
authors.initials: NA
authors.lastname: Caturello
authors.affiliation: Department of Biochemistry and Medical Chemistry, Medical School, University of Pécs , Szigeti 12, 7624 Pécs, Hungary.
authors.forename: Anikó
authors.initials: A
authors.lastname: Takátsy
authors.affiliation: Institute of Chemical Research of Catalonia (ICIQ) , Av. Països Catalans 16, 43007 Tarragona, Spain.
authors.forename: Gemma
authors.initials: G
authors.lastname: Aragay
authors.affiliation: Department of Inorganic Chemistry and MTA-PTE Research Group for Selective Chemical Syntheses, University of Pécs , Ifjúság 6, 7624 Pécs, Hungary.
authors.forename: László
authors.initials: L
authors.lastname: Kollár
authors.affiliation: São Carlos Institute of Chemistry, University of São Paulo , Av. Trab. São-carlense 400, 13560-970 São Carlos, SP, Brazil.|School of Pharmacy & Biomolecular Sciences, Liverpool John Moores University , Liverpool L3 3AF, United Kingdom.
authors.forename: Rodrigo Q
authors.identifier: 0000-0001-9064-4982
authors.initials: RQ
authors.lastname: Albuquerque
authors.affiliation: São Carlos Institute of Chemistry, University of São Paulo , Av. Trab. São-carlense 400, 13560-970 São Carlos, SP, Brazil.
authors.forename: Zsolt
authors.identifier: 0000-0001-9432-3879
authors.initials: Z
authors.lastname: Csók