Synthesis of Selenium Compounds by Free Radical Addition Based on Visible-Light-Activated Se-Se Bond Cleavage

化学 激进的 均分解 光化学 双键 区域选择性 共轭体系 键裂 有机化学 聚合物 催化作用
作者
Akihiro Nomoto,Yoshihiro Higuchi,Yohsuke Kobiki,Akiya Ogawa
出处
期刊:Mini-reviews in Medicinal Chemistry [Bentham Science]
卷期号:13 (6): 814-823 被引量:47
标识
DOI:10.2174/1389557511313060004
摘要

Upon irradiation with near-UV or visible light, organic diselenides undergo homolytic cleavage of their selenium-selenium linkage to generate the corresponding seleno radicals, which can add to alkynes, allenes, and related unsaturated compounds. In the case of alkynes, vicinally diselenated alkenes are synthesized successfully. Photoinduced bisselenation of allenes takes place selectively at the terminal double bond of allenes. In sharp contrast, photoinduced addition of organic diselenides to alkenes is an inefficient process. However, combination of diselenides and disulfides under photoirradiation conditions results in highly regioselective thioselenation of alkenes based on the higher reactivity of thio radicals toward alkenes and the higher carbon radical capturing ability of diselenides. Similar conditions can be employed with a variety of unsaturated compounds such as alkynes, allenes, conjugated dienes, vinylcyclopropanes, and isocyanides. This protocol can also be applied to selenotelluration, selenophosphination, and perfluoroalkylselenation of unsaturated compounds. The excellent carbon radical capturing ability of diselenides makes it possible to attain sequential addition of diselenides to several unsaturated compounds by suppression of polymerization of unsaturated compounds. When the sequential addition takes place intramolecularly under photoirradiation conditions, cyclic products are obtained successfully via a radical cyclization process. In addition, novel photoinduced electrocyclic reaction of o-alkynylaryl isocyanides with diselenides efficiently affords diselenated quinoline derivatives.
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