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School of Chemistry Colloquium: Dr Susannah Coote (Lancaster University) Making Difficult-to-Make Molecules: Photochemistry as an Enabling Tool

Converting simple starting materials into complex products using only a light source (synthetic photochemistry) is especially attractive to organic chemists, particularly from the point of view of green chemistry: waste is minimized, and light is readily available. In addition, photochemical routes often allow efficient access to complex frameworks (particularly to strained molecules and intermediates) that cannot be generated using ground-state chemistry.

We are particularly interested in the synthesis of four-membered rings, especially through the use of 4-pi-photocyclisations — reactions that are under-used by synthetic chemists.[1] For example, the 4-pi-photocyclisations of dihydropyridazines and tropone produce versatile cyclobutene products that can be converted into a variety of different derivatives.[2]

Our recent work directed at extending the synthetic potential of the Paternò-Büchi reaction will also be presented. Here, complex functionalised oxetane products are formed through the [2+2] photocycloaddition of maleic anhydride with cyclic ketones, and subsequent functionalisation provides access to a wide range of novel spirocyclic oxetane derivatives.

Coote, S. C. Eur. J. Org. Chem. 2020, 10, 1405.
Britten, T. K.; Kemmitt, P. D.; Halcovitch, N. R.; Coote, S. C. Org. Lett. 2019, 22, 9232.