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Scientific result | Chemistry
A team from SCBM, in collaboration with Mauritian modelers, has shown that carboxylic acids can be easily converted into small rings with four carbon atoms, the cyclobutanes, using blue LEDs and an iridium catalyst. Cyclobutanes are increasingly used in the design of new drugs and the method described here will help to significantly expand the chemical space explored in "drug discovery".
A new photoredox‐catalyzed decarboxylative radical addition approach to functionalized cyclobutanes is described. The reaction involves an unprecedented formal Giese‐type addition of C(sp3)‐centered radicals to highly strained bicyclo[1.1.0]butanes. The mild photoredox conditions, which make use of a readily available and bench stable phenyl sulfonyl bicyclo[1.1.0]butane, proved to be amenable to a diverse range of α‐amino and α‐oxy carboxylic acids, providing a concise route to 1,3‐disubstituted cyclobutanes. Furthermore, kinetic studies and DFT calculations unveiled mechanistic details on bicyclo[1.1.0]butane reactivity relative to the corresponding olefin system.
Ernouf G, Chirkin E, Rhyman L, Ramasami P, Cintrat JC. Photochemical Strain-Release-Driven Cyclobutylation of C(sp3 )-Centered Radicals. Angew Chem Int Ed Engl. 2019 http://dx.doi.org/10.1002/anie.201908951
CEA is a French government-funded technological research organisation in four main areas: low-carbon energies, defense and security, information technologies and health technologies. A prominent player in the European Research Area, it is involved in setting up collaborative projects with many partners around the world.