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  • Creating the Future

    The Hector Fellow Academy initiates innovative research projects on latest scientific problems.

Gold-catalyzed functionalization of 1,3-diyne derivatives

Philipp Stein – Hector Fellow A. Stephen K. Hashmi

The efficient design of chemical processes is of great importance for the chemical industry. Current research makes an essential contribution to synthesizing complex substrates inexpensively in as few steps as possible and in high yield. This PhD project, under the direction of Hector Fellow A. Stephen K. Hashmi, therefore, deals with the mechanism and the functionalization of a wide range of 1,3-diynes with varying nucleophiles.

The catalysis of organic reactions using transition metals is of immense importance for the chemical industry. Areas of application range from polymer chemistry to exhaust gas purification. The transition metal gold is also an interesting representative of a potential catalyst metal, since it has a high affinity for C-C - multiple bonds.

While numerous reactions with alkynes and allenes have been investigated in the past, the reaction behavior of 1,3-diyne compounds has only been researched to a small extent. This doctoral project therefore deals with the mechanism of monoaddition of a nucleophile to 1,3-diyne derivatives. With the help of this method, it is expected that complex substrates can be synthesized inexpensively in just a few steps. In addition, a further focus will be on the determination of reaction kinetics in order to characterize possible substituent effects of the substrate or the nucleophile and to unequivocally elucidate the mechanism taking place.

For this purpose, the required 1,3-diynes are first synthesized using a Glaser coupling and a test system is set up and optimized. This includes the parameters temperature, solvent, catalyst and the choice of nucleophile.

In the long term, this synthetic route is expected to offer favorable access routes to complex molecules. Possible approaches here are Diels-Alder reactions or the synthesis of novel polymers.

 

Scheme 1: Outlined reaction kinetics of substrates with varying substituents.