Supramolecular Assistance for the Selective Demethylation of Calixarene-Based Receptors

Pierre Edouard Danjou, Gaël De Leener, Damien Cornut, Steven Moerkerke, Samir Mameri, Angélique Lascaux, Johan Wouters, Andrea Brugnara, Benoit Colasson, Olivia Reinaud, Ivan Jabin

Research output: Contribution to journalArticlepeer-review


The selective demethylation of methoxy groups of several multifunctionalized 1,3,5-trimethoxycalix[6]arene-based receptors has been achieved. It is shown in this study that the best reagent is trimethylsilyl iodide (TMSI) and that the conformation adopted by the calixarene core is crucial for both the selectivity and the efficiency of the process. A key feature appears to be the "in" or "out" orientation of the methoxy substituents relative to the macrocyclic cavity. If projected inward, the reaction is slow and not selective. If projected outward, the reaction is fast and selective. A strategy that consists of exploiting the host-guest properties of the receptors to change their conformation and to permit their selective demethylation has been developed. Four cases of such a supramolecular assistance are reported, demonstrating the efficiency of the strategy. Such an allosteric control is highly reminiscent of biological processes allowing selective transformation of multifunctional molecules. (Figure Presented).

Original languageEnglish
Pages (from-to)5084-5091
Number of pages8
JournalJournal of Organic Chemistry
Issue number10
Publication statusPublished - 15 May 2015


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