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

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• 作者：Zoltán Nagymihály ; Naidel A. M. S. Caturello ; Anikó Takátsy ; Gemma Aragay ; László Kollár ; Rodrigo Q. AlbuquerqueZsolt Csók
• 刊名：Journal of Organic Chemistry
• 出版年：2017
• 出版时间：January 6, 2017
• 年：2017
• 卷：82
• 期：1
• 页码：390-396
• 全文大小：423K
• ISSN：1520-6904

文摘

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 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. Our experimental results along with thermodynamic energy analysis suggest that the observed self-sorting is a symmetry-driven, kinetically controlled process.