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(Reference retrieved automatically from Web of Science through information on FAPESP grant and its corresponding number as mentioned in the publication by the authors.)

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

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Author(s):
Nagymihaly, Zoltan ; Caturello, Naidel A. M. S. ; Takatsy, Aniko ; Aragay, Gemma ; Kollar, Laszlo ; Albuquerque, Rodrigo Q. ; Csok, Zsolt
Total Authors: 7
Document type: Journal article
Source: Journal of Organic Chemistry; v. 82, n. 1, p. 390-396, JAN 6 2017.
Web of Science Citations: 2
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 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)

FAPESP's process: 14/02071-5 - Theoretical investigation of the aggregation of cationic complexes of Ir(III) with potential application in LECs and OLEDs
Grantee:Rodrigo Queiroz de Albuquerque
Support type: Regular Research Grants