Pushing the boundaries of the nucleophilic aromatic substitution through photochemistry

Purpose and goal

The project had two goals; (i) to establish longterm research contacts between my research group at UU and AstraZeneca and (ii) to develop the photo-SNAr reaction. Both goals have been fulfilled; we have found further collaborative projects which have received external funding for three postdocs presently active on the projects and we have clarified the mechanism for the photo-SNAr reaction for pyrazines which enables us to consider other compound classes. The knowledge gained can be applied to understand why a certain class of drug molecules are light-sensitive.

Expected results and effects

The results from the studies of the photo-SNAr reaction were presented at two conferences; the IUPAC Photochemistry conference in Dublin in July this year, and a conference in Barcelona on Nov 1-2. We are writing on two manuscripts for research papers; one on the photo-SNAr reaction and on the photochemistry of dibenzannelated heterocycles with 8 pi-electrons (cores of psychopharmaca). A longterm collaboration with a series of domino effects has been established. The results from the three ongoing postdoc projects will lay the foundation for further papers and grant applications.

Planned approach and implementation

The time at AstraZeneca Gothenburg was split in 12 week-long visits, which essentially was optimal for the project implementation. It made it possible for a previous PhD student (Kjell Jorner, now postdoc at AZ Macclesfield) to participate in the project. Apart from the research collaboration I also gave a short lecture series on aromaticity effects in electronically excited states, with one lecture per month during Jan March this year. I have applied for funding from Stiftelsen Olle Engkvist Byggmästare for continued exchange, yet, with visits of one week every three months.