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首页> 美国卫生研究院文献>Molecules >Developments in Synthetic Application of Selenium(IV) Oxide and Organoselenium Compounds as Oxygen Donors and Oxygen-Transfer Agents
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Developments in Synthetic Application of Selenium(IV) Oxide and Organoselenium Compounds as Oxygen Donors and Oxygen-Transfer Agents

机译：氧化硒（IV）和有机硒化合物作为供氧体和氧转移剂的合成应用进展

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A variety of selenium compounds were proven to be useful reagents and catalysts for organic synthesis over the past several decades. The most interesting aspect, which emerged in recent years, concerns application of hydroperoxide/selenium(IV) oxide and hydroperoxide/organoselenium catalyst systems, as “green reagents” for the oxidation of different organic functional groups. The topic of oxidations catalyzed by organoselenium derivatives has rapidly expanded in the last fifteen years This paper is devoted to the synthetic applications of the oxidation reactions mediated by selenium compounds such as selenium(IV) oxide, areneseleninic acids, their anhydrides, selenides, diselenides, benzisoselenazol-3(2H)-ones and other less often used other organoselenium compounds. All these compounds have been successfully applied for various oxidations useful in practical organic syntheses such as epoxidation, 1,2-dihydroxylation, and α-oxyfunctionalization of alkenes, as well as for ring contraction of cycloalkanones, conversion of halomethyl, hydroxymethyl or active methylene groups into formyl groups, oxidation of carbonyl compounds into carboxylic acids and/or lactones, sulfides into sulfoxides, and secondary amines into nitrones and regeneration of parent carbonyl compounds from their azomethine derivatives. Other reactions such as dehydrogenation and aromatization, active carbon-carbon bond cleavage, oxidative amidation, bromolactonization and oxidation of bromide for subsequent reactions with alkenes are also successfully mediated by selenium (IV) oxide or organoselenium compounds. The oxidation mechanisms of ionic or free radical character depending on the substrate and oxidant are discussed. Coverage of the literature up to early 2015 is provided. Links have been made to reviews that summarize earlier literature and to the methods of preparation of organoselenium reagents and catalysts.
机译：在过去的几十年中，多种硒化合物被证明是有机合成的有用试剂和催化剂。近年来出现的最有趣的方面涉及氢过氧化物/氧化硒（IV）和氢过氧化物/有机硒催化剂体系的应用，作为氧化不同有机官能团的“绿色试剂”。在过去的十五年中，有机硒衍生物催化的氧化主题迅速发展。本文致力于硒化合物的介导氧化反应的合成应用，如氧化硒，芳硒酸，其酸酐，硒化物，二硒化物，苯并二硒唑-3（2H）-一和其他较不常用的其他有机硒化合物。所有这些化合物已成功应用于各种在实际有机合成中有用的氧化反应，例如烯烃的环氧化，1,2-二羟基化和α-氧官能化，以及环烷酮的环收缩，卤代甲基，羟甲基或活性亚甲基的转化生成甲酰基，将羰基化合物氧化为羧酸和/或内酯，将硫化物氧化为亚砜，将仲胺氧化为硝酮，并从其偶氮甲碱衍生物中再生母体羰基化合物。其他反应（例如脱氢和芳构化，活性碳-碳键裂解，氧化酰胺化，溴化，溴化和氧化反应，随后用于与烯烃的反应）也被氧化硒（IV）或有机硒化合物成功地介导了。讨论了取决于底物和氧化剂的离子或自由基特性的氧化机理。提供了截至2015年初的文献报道。已经建立了链接，这些链接总结了较早的文献，以及有机硒试剂和催化剂的制备方法。

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