Green Approach to a Problematic Transformation in Organic Synthesis

We intend to build up knowledge on how alcohols can be used as a carbon feedstock for future chemical production by studying the reaction mechanism of the key step in detail.

Our hypothesis is: If the C-O bond in the alcohol can be weakened by the acidic part of a catalyst [A] and at the same time the nucleophile (the molecule to react with the alcohol) is activated by partial deprotonation by the basic part of the catalyst [B], the substitution of an alcohol is possible.

Noteworthy, the only by-product from this reaction is water.

This dual activation by the catalyst will be studied separately with different methods where NMR techniques will be prominent. Specifically, the C-O bond weakening by [A] will be monitored by 13C NMR spectroscopy.

The activation by the catalyst will be evaluated in substitution reactions of the hydroxyl group in stereogenic alcohols where the stereospecificity from the starting material to the product will be monitored. Kinetics and kinetic isotope effects will be measured to verify reaction mechanisms.

Both the free sites [A] and [B] of the catalyst will be used as a catalytic system as well as designed catalysts in which the [A] and [B] are linked together.

The importance of the research is both the fundamental aspects where C-O bond activation in alcohols is still not understood as well as this basic research is essential for transforming our society towards a bio-economy in a not too distant future.