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

Nagymihály, Z and caturello, NAMS and Takátsy, A and Aragay, G and Kollár, L and Queiroz De Albuquerque, R and Csok, Z (2016) Palladium-Mediated Catalysis Leads to Intramolecular Narcissistic Self-Sorting on a Cavitand Platform. Journal of Organic Chemistry. ISSN 0022-3263

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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, no ‘mixed’ products possessing structurally different amide fragments are detected either by 1H or 13C 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. The reactivity order of the amine reactants and the changes in the Gibbs energies calculated using the semiempirical PM6 model suggest that this self-sorting process is kinetically controlled.

Item Type: Article
Uncontrolled Keywords: 0304 Medicinal And Biomolecular Chemistry, 0305 Organic Chemistry, 0302 Inorganic Chemistry
Subjects: Q Science > QD Chemistry
Divisions: Pharmacy & Biomolecular Sciences
Publisher: American Chemical Society
Date Deposited: 19 Dec 2016 11:58
Last Modified: 07 Sep 2017 13:12
DOI or Identification number: 10.1021/acs.joc.6b02472
URI: http://researchonline.ljmu.ac.uk/id/eprint/5117

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