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Scientific result | Chemistry

Light to release the tension of cycles


​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".

Published on 3 December 2019

Abstract

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.

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