New Methods for the Formation of Carbon-Carbon Bonds from Alcohols
Currently, most chemicals are produced using fossil resources as feedstock. Due to the expected limited availability of these resources in the future, new focus has been put on the synthesis of chemicals from renewable feedstocks, such as biomass. In contrast to fossil fuels containing mainly hydrocarbons, biomass derived chemicals contain a high amount of alcohols. It is therefore of high interest to develop new methods to transform these compounds, creating the need for more reactions using alcohols as the starting materials.
In this thesis, a new reaction was developed using benzylic alcohols for the synthesis of stilbenes from arylacetonitriles under basic conditions. The scope of the reaction was then broadened by the introduction of a simple two-step protocol, allowing for the use of benzylic halides as starting materials, which are more commonly available than arylacetonitriles.
A second project focused on the valorization of ethylene glycol, a platform chemical that can be synthesized from cellulose. The newly developed method enables the formation of a carbon-carbon bond between ethylene glycol and various olefins by employing blue light to activate the used catalyst.
During a project performed at Lundbeck a new bioisostere of the phenyl ring (oxaBCO) was investigated, since pharmaceutical companies are interest in introducing bioisosteres, which are three dimensional because an increased three dimensionality can improve the properties of a drug. The investigated bioisostere was incorporated into known drugs, Resveratrol, Benzocaine, and Leteprinim to compare the properties of the synthesized analogues to those of the parent compound and validate oxaBCO as a bioisostere of the phenyl ring.
Principal Supervisor:
Professor Robert Madsen, DTU Chemistry
Co-supervisor:
Professor Mads H. Clausen, DTU Chemistry
Examiners:
Associate Professor Luca Laraia, DTU Chemistry
Professor Kenneth Wärnmark, Lund University, Sweden
Professor Thomas B. Poulsen, Aarhus University
Chairperson:
Associate Professor Sebastian Meier, DTU Chemistry