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Article

Ambiphilic Frustrated Lewis Pair Exhibiting High Robustness and Reversible Water Activation: Towards the Metal-Free Hydrogenation of Carbon Dioxide

by
Étienne Rochette
1,
Marc-André Courtemanche
1,
Alexander P. Pulis
2,
Wenhua Bi
1 and
Frédéric-Georges Fontaine
1,*
1
Department of Chemistry, Centre de Catalyse et Chimie Verte (C3V), Université Laval, 1045 Avenue de la Médecine, Québec, QC G1V 0A6, Canada
2
Department of Chemistry, University of Toronto, 80 George Street, Toronto, ON M5S 3H6, Canada
*
Author to whom correspondence should be addressed.
Molecules 2015, 20(7), 11902-11914; https://doi.org/10.3390/molecules200711902
Submission received: 21 April 2015 / Revised: 4 June 2015 / Accepted: 19 June 2015 / Published: 29 June 2015
(This article belongs to the Special Issue The Reactivity of Frustrated Lewis Pairs)
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Abstract

The synthesis and structural characterization of a phenylene-bridged Frustrated Lewis Pair (FLP) having a 2,2,6,6‑tetramethylpiperidine (TMP) as the Lewis base and a 9-borabicyclo[3.3.1]nonane (BBN) as the Lewis acid is reported. This FLP exhibits unique robustness towards the products of carbon dioxide hydrogenation. The compound shows reversible splitting of water, formic acid and methanol while no reaction is observed in the presence of excess formaldehyde. The molecule is incredibly robust, showing little sign of degradation after heating at 80 °C in benzene with 10 equiv. of formic acid for 24 h. The robustness of the system could be exploited in the design of metal-free catalysts for the hydrogenation of carbon dioxide.
Keywords: carbon dioxide; Frustrated Lewis Pairs; hydrogenation; Lewis acid; ambiphilic molecules; catalysis carbon dioxide; Frustrated Lewis Pairs; hydrogenation; Lewis acid; ambiphilic molecules; catalysis

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MDPI and ACS Style

Rochette, É.; Courtemanche, M.-A.; Pulis, A.P.; Bi, W.; Fontaine, F.-G. Ambiphilic Frustrated Lewis Pair Exhibiting High Robustness and Reversible Water Activation: Towards the Metal-Free Hydrogenation of Carbon Dioxide. Molecules 2015, 20, 11902-11914. https://doi.org/10.3390/molecules200711902

AMA Style

Rochette É, Courtemanche M-A, Pulis AP, Bi W, Fontaine F-G. Ambiphilic Frustrated Lewis Pair Exhibiting High Robustness and Reversible Water Activation: Towards the Metal-Free Hydrogenation of Carbon Dioxide. Molecules. 2015; 20(7):11902-11914. https://doi.org/10.3390/molecules200711902

Chicago/Turabian Style

Rochette, Étienne, Marc-André Courtemanche, Alexander P. Pulis, Wenhua Bi, and Frédéric-Georges Fontaine. 2015. "Ambiphilic Frustrated Lewis Pair Exhibiting High Robustness and Reversible Water Activation: Towards the Metal-Free Hydrogenation of Carbon Dioxide" Molecules 20, no. 7: 11902-11914. https://doi.org/10.3390/molecules200711902

APA Style

Rochette, É., Courtemanche, M.-A., Pulis, A. P., Bi, W., & Fontaine, F.-G. (2015). Ambiphilic Frustrated Lewis Pair Exhibiting High Robustness and Reversible Water Activation: Towards the Metal-Free Hydrogenation of Carbon Dioxide. Molecules, 20(7), 11902-11914. https://doi.org/10.3390/molecules200711902

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