Description
Great attention is currently being paid to the development of efficient metal catalyzed processes because the current synthesis in both laboratories and in industry often relies on these synthetic transformations. The main research goals can be seen in the design of brand new reactions, in increasing the efficiency of the known processes and also in reduction of their environmental impact. The objective of this project objective is to develop, synthesize and test new polar phosphine ligands suitable for use as catalyst in palladium-mediated C–C bond forming reactions that can be performed in water or aqueous reaction media. To this end, the structures of selected lead donors will be modified by hydrophilic tags to ensure their affinity toward water and the prepared compounds will be evaluated in practically important cross-coupling reactions. The project builds upon synergy between theoretical approach toward investigating chemical reactions and properties of the relevant compounds (in silico design), and the classical synthetic approach, which are guaranteed by the participating laboratories from the University of Bergen and Charles University in Prague.
Summary of project results
The main objective of the ENVIPHOS project was the design of new polar donors by using the conventional and automated computer-aided approaches that were previously studied by the Czech and Norwegian team, respectively. The project aims were achieved though in a limited extent because the project was started with a substantial delay. Several compound classes including the real donors and model compounds were synthesized by the Czech team and thoroughly characterized by means of a range of physicochemical, electrochemical and theoretical methods with an aim of determining their steric and electronic properties and also factors that determine them. The collected results were supplemented by extensive catalytic testing in Pd-catalyzed C-C bond forming reactions and the catalytic results were correlated with the available characterization data and the results of theoretical investigation of the reaction mechanism. Altogether, the project resulted so far in 3 papers published in or submitted to peer-reviewed scientific journals, several conference contributions and one bachelor degree thesis (P. Měrka – Charles University). Further papers are currently being prepared and conference contributions will follow. From a wider perspective, the results can serve as a sound basis for the future design of new donors suitable for applications as supporting ligands for Pd-mediated reactions performed in aqueous reaction media and thus lower the impact of these processes on the environment.
Summary of bilateral results
The proposed grant project was based on sharing expertise of the participating teams, which was accomplished. The Czech team benefited mostly from implementation of new theoretical approaches, while the Norwegian partner advantageously utilized the results and ideas of the members of the Czech team in improving their computational approach toward ligand design. The Norwegian partner team contributed an extensive computational investigation of reaction mechanism of the palladium-catalyzed cross coupling using ligands of the kind developed by the Czech team. This investigation gives insight useful for design of improved ligands. Moreover, the Norwegian team prepared for automated in silico design of ligands and catalysts. The project resulted in one joint paper summarizing DFT investigations into the mechanism of the reactions studied during solving the grant project. The collaboration opened possibilities of future collaboration exploiting the truly complementary knowledge of the teams that participated in this grant project. The project has no immediate impact on or benefit to the general society. However, its results can help in advancing the design of new efficient ligands suitable for synthetically important Pd-catalyzed processes performed in green reaction media and thus minimize the impact of these processes on the environment.