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

Résultats de recherche: Contribution à un journal/une revueArticle

Résumé

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).

langue originaleAnglais
Pages (de - à)5084-5091
Nombre de pages8
journalJournal of Organic Chemistry
Volume80
Numéro de publication10
Les DOIs
étatPublié - 15 mai 2015

Empreinte digitale

Calixarenes
Conformations
Molecules

Citer ceci

Danjou, P. E., De Leener, G., Cornut, D., Moerkerke, S., Mameri, S., Lascaux, A., ... Jabin, I. (2015). Supramolecular Assistance for the Selective Demethylation of Calixarene-Based Receptors. Journal of Organic Chemistry, 80(10), 5084-5091. https://doi.org/10.1021/acs.joc.5b00464
Danjou, Pierre Edouard ; De Leener, Gaël ; Cornut, Damien ; Moerkerke, Steven ; Mameri, Samir ; Lascaux, Angélique ; Wouters, Johan ; Brugnara, Andrea ; Colasson, Benoit ; Reinaud, Olivia ; Jabin, Ivan. / Supramolecular Assistance for the Selective Demethylation of Calixarene-Based Receptors. Dans: Journal of Organic Chemistry. 2015 ; Vol 80, Numéro 10. p. 5084-5091.
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Danjou, PE, De Leener, G, Cornut, D, Moerkerke, S, Mameri, S, Lascaux, A, Wouters, J, Brugnara, A, Colasson, B, Reinaud, O & Jabin, I 2015, 'Supramolecular Assistance for the Selective Demethylation of Calixarene-Based Receptors', Journal of Organic Chemistry, VOL. 80, Numéro 10, p. 5084-5091. https://doi.org/10.1021/acs.joc.5b00464

Supramolecular Assistance for the Selective Demethylation of Calixarene-Based Receptors. / Danjou, Pierre Edouard; De Leener, Gaël; Cornut, Damien; Moerkerke, Steven; Mameri, Samir; Lascaux, Angélique; Wouters, Johan; Brugnara, Andrea; Colasson, Benoit; Reinaud, Olivia; Jabin, Ivan.

Dans: Journal of Organic Chemistry, Vol 80, Numéro 10, 15.05.2015, p. 5084-5091.

Résultats de recherche: Contribution à un journal/une revueArticle

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T1 - Supramolecular Assistance for the Selective Demethylation of Calixarene-Based Receptors

AU - Danjou, Pierre Edouard

AU - De Leener, Gaël

AU - Cornut, Damien

AU - Moerkerke, Steven

AU - Mameri, Samir

AU - Lascaux, Angélique

AU - Wouters, Johan

AU - Brugnara, Andrea

AU - Colasson, Benoit

AU - Reinaud, Olivia

AU - Jabin, Ivan

PY - 2015/5/15

Y1 - 2015/5/15

N2 - 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).

AB - 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).

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Danjou PE, De Leener G, Cornut D, Moerkerke S, Mameri S, Lascaux A et al. Supramolecular Assistance for the Selective Demethylation of Calixarene-Based Receptors. Journal of Organic Chemistry. 2015 mai 15;80(10):5084-5091. https://doi.org/10.1021/acs.joc.5b00464