ISCR  Laboratory

The Rennes teams aim at developing a competitive organometallic homogeneous catalysis and molecular valorization of renewable raw materials including carbohydrates, oilseeds and lignin. Another important activity deals with the conception and preparation of green surfactants based on renewable raw materials (from marine resources, carbohydrates, glycerol…). These sustainable chemistry research areas are directed toward the development of efficient and selective, synthetic methodologies and the target-oriented preparation of platform molecules of industrial relevance. The researches in our groups are devoted to efficient transition metal catalyzed metathesis of oils, reduction of carboxylic derivatives, C-H bond functionalization of aromatic (including furans) and hydrocarbon derivatives, polymerization of biomonomers, innovative preparation of green and biodegradable surfactants, structural modulations of carbohydrates according to chemical and/or chemo-enzymatic approaches.

The homogeneous catalysis team at ISCR has by its size and international visibility a unique place in French chemical research. One essential expertise of the team is the homogeneous organometallic catalysis engineering directed toward fine chemistry and polymer science. A special focus is placed on the substitution of noble, heavy metals by earth-abundant, inexpensive and benign transition and main-group metal catalysts based on  iron, manganese, calcium, etc.
Another recognized expertise lies in the field of glycochemistry, biocatalysis and synthesis of fully-biosourced surfactants for cosmetics or detergents. This also includes determination of the physicochemical properties of the neo-amphiphiles and elucidation of structure/properties relationships.


The methodologies developed in our groups are:

  • Catalytic transformations in water and green solvents for C-H bond activation/functionalization of (hetero)aromatics including furans,  using palladium, ruthenium or earth-abundant transition metals
  • Catalyzed reductions (hydrogenation, hydrogen autotransfer, hydrosilylation) of polyfunctional molecules derived from biomass (carboxylic acids and esters, fatty acids, furan derivatives…) for the preparation of alcohol and amine synthons.
  • Transformation of renewables (oils, terpenes, agro-sourced terminal olefins from Fischer-Tropsch feeds, etc.) and bulk commodities using olefin metathesis reactions (RCM, ROMP, CM, ADMET); Catalytic cascade or tandem reactions;
  • Organometallic catalysis based on oxophilic elements (groups 2-6, 13): hydroelementations, dehydrogenative cross-couplings, etc.
  • Biosourced monomers & polymers via catalysis; Macromolecular engineering for new (bio)materials
  • Nanocatalysis and oxidation
  • Structural modulations of biomass: PHA, triglycerides, mono- and polysaccharides (depolymerization, conjugation), by-products from biomass extraction, malic acid (for nanoparticules); Applications in detergency, cosmetic, health (vectorization of drugs)
  • Biocatalysis of improvement of biocatalysts thanks to molecular biology tools

Selected industrial applications:

One start-up, OmegaCatSystem, dedicated to innovative catalytic processes based on olefin metathesis (creation 2010).
A business unit Surfact’Green, dedicated to the production and formulation of biobased surfactants.


Selected publications (2014-2015)

  • Iron-catalyzed C-H borylation of arenes, J.-B. Sortais, C. Darcel, J. Am. Chem. Soc. 2015, 137, 4062.
  • Hydrosilylation of aldehydes and ketones catalyzed by Mn(I)-NHC complexes, J.-B. Sortais, C. Darcel, Adv. Synth. Catal. 2014, 356, 1093.
  • Terminal conjugated dienes via ruthenium-catalyzed cross-metathesis /elimination sequence: application to renewable resources, C. Fischmeister, C. Bruneau, Catal. Sci. Technol. 2014, 4, 2064.
  • Cross-metathesis of fatty acid methyl esters with acrolein: An entry to a variety of bifunctional compounds, C. Fischmeister, C. Bruneau, Eur. J. Lipid Sci. Technol. 2015, 117, 209.
  • Functionalization of C–H bonds via metal-catalyzed desulfitative coupling: alternative tool for access to aryl- or alkyl-substituted (hetero)arenes, J.-F. Soulé, H. Doucet, ACS Catal., 2015, 5, 978.
  • Ecofriendly solvents for palladium-catalyzed desulfitative C–H Bond arylation of heteroarenes, J.-F. Soulé, H. Doucet ChemSusChem, 2015, 8, 1794
  • Barium-mediated cross-dehydrocoupling of hydrosilanes with amines - J.-F. Carpentier, Y. Sarazin, Angew. Chem. Int. Ed. 2015, 54, 7679. 
  • Highly stereocontrolled ring-opening polymerization of racemic-Alkyl -malolactonates mediated by yttrium complexes, E. Kirillov, J.-F. Carpentier, S. Guillaume, Chem. Eur. J. 2016, 22, DOI: 10.1002/chem.201600223R1.
  • Highly selective cycloalkanes oxidation in water with ruthenium nanoparticles. A. Denicourt-Nowicki, A. Roucoux, ChemCatChem, 2016, 8, 357.
  • Magnetically retrievable Rh(0) nanocomposite as catalyst for mild hydrogenation of functionalized arenes in water, A. Denicourt-Nowicki, A. Roucoux, ACS Sustainable Chem. Eng., 2016, 4, 1834
  • Process for metathesis of olefins obtained from Fischer-Tropsch fractions using a ruthenium dissymmetrical N-heterocyclic diaminocarbene complex. M. Mauduit - U.S. Pat. Appl. Publ. (2014), US 20140323671
  • From algal polysaccharides to cyclodextrins to stabilize a urease inhibitor
    C. Nugier-Chauvin, , D. Wolbert, V. Ferrieres, et al. Carbohydr. Polym. (2014), 112, 145.
  • Glycosylation of aryl pyranosides and aryl/alkyl furanosides demonstrating the versatility of thermostable CGTase from Thermoanaerobacterium sp
    V. Ferrieres, C. Nugier-Chauvin, et al., Green Chem. (2014), 16, 3803.
  • Araf51 with improved transglycosylation activities: one engineered biocatalyst for one specific acceptor
    C. Nugier-Chauvin, V. Ferrieres, et al. Carbohydr. Res. (2015), 402, 50.
  • Bio-based polyester materials from vegetable oil and short to long chain dicarboxylic acids
    J.-L. Audic, L. Lemiègre, et al. Indust. Crops Prod. (2015), 70, 213.
  • A cationic emulsifying composition for cosmetic uses
    T. Benvegnu, L. Lemiegre, et al., PCT Int. Appl. (2015), WO 2015078890 A1 20150604.
  • Cosmetic compositions comprising alkyl polyglucosides and fatty esters of cationic amino acids
    T. Benvegnu, et al. PCT Int. Appl. (2015), WO 2015078893 A1 20150604
  • Interactions and hybrid complex formation of anionic algal polysaccharides with a cationic glycine betaine-erived surfactant
     T. Benvegnu, et al. Carbohydr. Polym. (2015), 121, 436.
  • Glycolipid-based nanosystems for the delivery of drugs, genes and vaccine adjuvant applications
    T. Benvegnu, L. Lemiegre, D. Plusquellec, et al., Carbohydr. Chem. (2014) 40, 341.

 

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