Electrochemical cyclization of unsaturated hydroxy compounds. Phenylselenoetherification and phenylselenolactonization

Electrochemical synthesis of organic selenium and tellurium compounds as well as different mechanisms of their anodic and cathodic reactions were reviewed. The first part includes the review of the direct synthesis of the title compounds from the elemental selenium and tellurium, the synthesis by anodic reactions using mainly the generation of arylselenium or tellurium cations and the cathodic reduction based on the generation of organoselenium and tellurium anions. These synthetic applications, more interesting for the wider group of organic chemists, are discussed in more detail. Examples of the anodic functionalization (such as acetoxylation or fluorination) leading to new organic chalcogen compounds are also given. The detailed discussion of the anodic behavior of the title compounds is divided into separate parts, each of them devoted to the different class of compounds. They include first of all diaryl, dialkyl and alkylarylselenides and tellurides, most widely investigated for many years, and next diaryl and dialkyl diselenides. However, anodic reactions of some typical heterocyclic selenides and tellurides are also briefly reviewed. Some electrode reactions in which the title compounds play only the role of intermediates are mentioned as well. Finally, electroreduction mechanisms of organoselenium and tellurium compounds are discussed.

Section: B Synthesis By Anodic Reactionsmentioning

confidence: 95%

Section: B Synthesis By Anodic Reactionsmentioning

confidence: 99%

Section: B Synthesis By Anodic Reactionsmentioning

confidence: 99%

Section: B Synthesis By Anodic Reactionsmentioning

confidence: 99%

Section: B Synthesis By Anodic Reactionsmentioning

confidence: 99%

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Selenium moieties are conveniently introduced into an organic molecule using electrophilic selenenylating reagents and the process is generally highly chemo‐, regio and stereoselective requiring mild experimental conditions. In addition, organoselenium derivatives can be directly converted into a number of different functional groups and the organoselenium moiety can be employed for further stereoselective manipulation of the molecule. Several applications are described for the inter‐ and intramolecular carbon–oxygen, carbon–nitrogen and carbon–carbon bond formation as well as for the α‐functionalization of carbonyl derivatives and the nucleophilic aromatic substitution reactions. More recently, the development of simple and efficient procedures for the preparation of chiral selenium reagents allowed their successful application in electrophilic asymmetric synthesis. Nowadays, probably the most recent aspect of this kind of chemistry is correlated with some new reactions that can be effected using organoselenium compounds as catalysts in renewable or alternative non‐toxic media (water, glycerol, ionic liquids) bringing this kind of research in line with the concept of ‘Green and Sustainable Chemistry’. During the last half century, the application of tellurium reagents has undergone a notable improvement, overcoming the reluctance of several researchers mainly due to the characteristic persistent smell of many tellurium derivatives. In this chapter some general aspects of the chemistry promoted by electrophilic selenium and tellurium compounds are described exploiting also the differences between these two reagents.