1285523-48-9Relevant academic research and scientific papers
Finding furfural hydrogenation catalysts via predictive modelling
Strassberger, Zea,Mooijman, Maurice,Ruijter, Eelco,Alberts, Albert H.,Maldonado, Ana G.,Orru, Romano V. A.,Rothenberg, Gadi
supporting information; experimental part, p. 2201 - 2210 (2010/11/05)
We combine multicomponent reactions, catalytic performance studies and predictive modelling to find transfer hydrogenation catalysts. An initial set of 18 ruthenium-carbene complexes were synthesized and screened in the transfer hydrogenation of furfural to furfurol with isopropyl alcohol complexes gave varied yields, from 62% up to >99.9%, with no obvious structure/activity correlations. Control experiments proved that the carbene ligand remains coordinated to the ruthenium centre throughout the reaction. Deuterium-labelling studies showed a secondary isotope effect (kH:kD = 1.5). Further mechanistic studies showed that this transfer hydrogenation follows the so-called monohydride pathway. Using these data, we built a predictive model for 13 of the catalysts, based on 2D and 3D molecular descriptors. We tested and validated the model using the remaining five catalysts (cross-validation, R2 = 0.913). Then, with this model, the conversion and selectivity were predicted for four completely new ruthenium-carbene complexes. These four catalysts were then synthesized and tested. The results were within 3% of the model's predictions, demonstrating the validity and value of predictive modelling in catalyst optimization.
A facile route to ruthenium-carbene complexes and their application in furfural hydrogenation
Strassberger, Zea,Mooijman, Maurice,Ruijter, Eelco,Alberts, Albert H.,De Graaff, Corien,Orru, Romano V.A.,Rothenberg, Gadi
experimental part, p. 142 - 146 (2010/11/19)
A number of new N-heterocyclic carbene (NHC) ligands were synthesized via a multicomponent reaction, wherein an aldehyde or ketone, a primary amine and an a-acidic isocyanide were reacted, giving the corresponding 2H-2-imidazolines. These were easily alkylated with an alkyl halide at position N-3, yielding the final NHC precursors, that were then complexed with Ru in situ. The resulting complexes are shown to be active and selective catalysts for the transfer hydrogenation of furfural to furfurol, using isopropanol as the hydrogen source. Importantly, the carbene ligand remains coordinated to the ruthenium center throughout the reaction. Copyright
