Annual Scientific Report 2013

A process for the direct cupration of fluoroform has been developed. This exceedingly simple process employs only cheap reagents and is advantageously run at room temperature to produce CuCF₃ reagents that are useful in trifluoromethylation reactions. Chemical compounds bearing a trifluoromethyl group are widely used in the production of various pharmaceuticals and agrochemicals as well as specialty materials, polymers, composites, building blocks, and intermediates for various needs. Fluoroform, CF₃H, is an ideal source of CF₃ because it is inexpensive, readily available in large industrial quantities, non‐toxic, and not an ozone depleter.

Conversion of biomass into high value materials is one of the challenges the chemical industry is facing. This technology, based on a two-step synthesis (benzoin condensation followed by asymmetric transfer hydrogenation) allows preparing in high yields and selectivity a stable chiral hydrofuroin derivative which may serve as building block for new ligands, active ingredients or polymers, among other applications of chiral 1,2-diols.

Chemical reduction of carbon dioxide to methanol and its derivatives (such as DME) is considered one of the key technologies to reduce both global warming and fossil fuels dependency. Unlike the currently used process for methanol synthesis, ICIQ’s process provides excellent conversions and selectivity to methanol in one pass through the reactor, thereby providing the highest time yield observed for the chemical reduction of CO₂.

Quinine and quinidine (natural products), can be transformed into eight structurally different compounds useful in organocatalysis and cascade processes of enolizable compounds. The synthesis allows for the conservation of the chiral centers. The obtained compounds, cinchona alkaloid derivatives, can be used as metal-free catalysts for the preparation of complex scaffolds in a limited number of steps within cascade reactions. Other applications include asymmetric Michael additions, fluorination of ketones, etc.

A nanoparticle containing two different populations of chromophores and funcionalized with a dye-labelled peptide sensitive to the action of a hydrolytic enzyme has been developed. In that way, the optical response of the system can directly be correlated, in a quantitative manner, to the activity of a specific enzyme found in the medium where the nanoparticle is placed, thereby allowing for enzyme quantification.  This technology was applied to cystic fibrosis, through the analysis of the trypsin amount of faeces samples. It was shown that this system could allow for the determination of patient’s phenotype, thus avoiding genetic testing.

A family of compounds able to form a network of rings interconnected by rods at the micro/nanoscopic scale through a self-assembly process has been developed. These compounds could successfully be incorporated into plastic materials in which the characteristic assembly is conserved. Within a polymer matrix containing carbon materials such as carbon nanotubes (composite material), the carbon particles aggregate around the self-assembled network, forming a network of dispersed and interconnected carbon materials, giving rise to e.g. lower percolation thresholds.

3-indolylmethanamines, and more particularly their chiral derivatives, constitute a relevant family of compounds for the crop protection and pharmaceutical industries. The invention provides a polymer-supported organocatalysts that is highly active and selective for the preparation of such compounds by Friedel-Crafts reactions. Being supported on a polystyrene resin, the catalyst is easily recyclable by filtration and can be used under continuous flow conditions, making it suitable for process intensification and the preparation of libraries of chiral compounds.