Green chemistry and catalysis

Keywords : Organocatalysis, Supramolecular Activation, Hydrogen-Bonding Catalyst, Copper-based Catalysis, Photoactivable Catalysts, Click Chemistry, Asymmetric Aldol Processes, Fluorous Catalysis

Contacts :

Bibal, Brigitte ; Desvergne, Jean-Pierre ; Lastécouères, Dominique ; Vincent, Jean-Marc

We are interested in the development of new, environmentally friendly methodologies which are of practical value for important chemical transformations.

In collaboration with polymer specialists (LCPO, UMR 5629), we developed different Hydrogen-bonding catalysts (Amide, phenol, ammonium derivatives) for Ring-Opening Polymerization (ROP) of cyclic esters (Lactide, Valerolactone and Caprolactone). Through a controlled process, the catalytic systems induced a full conversion in 24 h, under simple conditions. Currently, new supramolecular systems are developed for different organic reactions.

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We also developed a proline-based catalyst (BIP) for asymmetric aldol processes that we applied to the straightforward synthesis of chiral lactons (isotetronic acids) and alcaloids (indolizidines). Ongoing research in this area deals with the application of such organocatalyzed processes for the preparation of chiral polymers (ANR program "CHIRPOL" 2009-2012, PI : Prof H. Cramail, LCPO, UMR 5629).

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Another research interest is the search for highly reactive copper-based catalysts, in particular for applications in radical polymerizations (ATRP) and click chemistry. We recently reported that copper catalyst activation could be driven through a photoinduced electron transfer (PET) process. This was the first example of a photoactivable click catalyst.

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Selected Publications : 

Supramolecular Catalysis for Ring-Opening reactions :

1/ Ring-Opening Polymerization of L -Lactide Efficiently Triggered by an Amido-Indole. X-ray Structure of a Complex between L-Lactide and the Hydrogen-Bonding Organocatalyst S. Koeller, J. Kadota, A. Deffieux, F. Peruch, S. Massip, J.-M. Léger, J.-P. Desvergne,* B. Bibal,* J. Am. Chem. Soc. 2009, 131, 15088-15089. Click Here

2/ (Thio)amido-Indoles and (Thio)amido-Benzimidazoles : an Investigation of their Hydrogen-bonding and Organocatalytic Properties in the Ring Opening Polymerization of Lactide S. Koeller, J. Kadota, F. Peruch, A. Deffieux, N. Pinaud, I. Pianet, S. Massip, J.-M. Léger, J.-P. Desvergne, B. Bibal,* Chem. Eur. J. 2010, 16, 4196-4205. Click Here

3/ Phenols and Tertiary Amines : An Amazingly Simple Hydrogen-Bonding Organocatalytic System Promoting Opening Polymerization C. Thomas, F. Peruch, A. Deffieux, A. Milet, J.-P. Desvergne, B. Bibal,* Adv. Synth. & Catalysis 2011, 353, 1049-1054. Click Here

4/ Ring-Opening Polymerization of Lactones using Supramolecular Organocatalysts Under Simple Conditions C. Thomas, F. Peruch,* B. Bibal,* RSC Adv. 2012, DOI:10.1039/C2RA22535B. Click Here

Organocatalyzed aldol processes and copper catalysis :

Copper catalyst activation driven by photoinduced electron transfer : A prototype photolatent click catalyst, L. Harmand, S. Cadet, B. Kauffmann, L. Scarpantino, P. Batat, G. Jonusauskas, D. Lastécouères, J.-M. Vincent,* Angew. Chem. Int. Ed., 2012, 51, 7137. (selected as “Very Important Paper”) Click Here

Fluorous catalysis : From the origin to recent advances J.-M. Vincent, Top. Curr. Chem. 2012, 308, 153. Click Here

A highly active and reusable copper(I)-tren catalyst for the “click” 1,3-dipolar cycloaddition of azides and alkynes N. Candelon, D. Lastécouères, A. Khadri Diallo, J. Ruiz Aranzaes, D. Astruc, J.-M. Vincent*, Chem. Commun. 2008, 741. Click Here

Closer to the « ideal recoverable catalyst” for atom transfer radical polymerisation using a molecular non-fluorous thermomorphic system G. Barré, D. Taton, D. Lastécouères,* J.-M. Vincent,* J. Am. Chem. Soc. 2004, 126, 7764. Click Here

A concise organocatalytic and enantioselective synthesis of isotetronic acids J.-M. Vincent,* C. Margottin, M. Berlande, D. Cavagnat, T. Buffeteau, Y. Landais,* Chem. Commun. 2007, 4782. Click Here

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