Abstract
AbstractEthylene glycol is produced on a very large industrial scale and is used for the preparation of polyesters and antifreeze formulations. Although the diol is mainly manufactured from fossil‐based resources, new commercial procedures from carbohydrates are currently being introduced, which eventually will make ethylene glycol an important bio‐derived compound in organic chemistry. However, further transformations of the diol for the formation of carbon─carbon bonds have so far received relatively little attention. In the present work, the photocatalyzed coupling between ethylene glycol and electron‐deficient olefins is therefore investigated. The results show that an iridium complex can be employed to mediate the reaction with acrylates, acrylamides, acrylonitriles, and vinyl sulfones to generate a range of chain‐elongated lactones and diols. Substituents are tolerated in the α position of acrylates while a poor outcome is obtained with substituents in the β position of the electron‐deficient olefin. The results illustrate the formation of new carbon─carbon bonds from an abundant alcohol by the use of photocatalytic transformations.
Published Version
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