Synthetic and Mechanistic Studies on Ni-catalysed Benzannulation Reactions

• Applicant: Dr. Timo Stalling
• Subject Area: Organic Molecular Chemistry - Synthesis and Characterisation
• Term: from 2013 to 2014
• Project identifier: Deutsche Forschungsgemeinschaft (DFG) - Project number 250786160

Aromatic compounds play a leading role in all aspects of the scientific and common environment (e.g. natural and smart materials). Therefore, this proposal seeks to grow Ni-catalysed cycloadditions of alkynes as an efficient and atom economic method for the synthesis of boronates, which are synthetically powerful components for the formation of aromatic and analogous heterocyclic compounds. The remarkable advantage of this process is the use of relatively simple starting materials which allow to construct complex and heavily substituted structures.Predominantly, the reaction mechanism of the Ni-catalysed benzannulation of cyclobutenones should be established by using donor functionalized alkynes. With these mechanistic insights, substrates that offer consistently high levels of regioselectively in the benzannulation reaction should be designed. This step would be a key milestone for Ni-catalysed benzannulation.Finally, the available toolbox of Ni-catalysed reactions should be significantly expanded to aromatic and analog heterocyclic boronates (e. g. carbonyl compounds containing nitrogen or oxygen) which have not yet been prepared by transition metal catalysis. Due to their manifold downstream chemistry a particular focus will be on the preparation of polycyclic compounds that cannot be accessed using the current methodology.

• DFG Programme: Research Fellowships
• International Connection: United Kingdom
• Host: Professor Joseph P. A. Harrity