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Iodonium Cation‐Pool Electrolysis for the Three‐Component Synthesis of 1,3‐Oxazoles
Chemistry - A European Journal ( IF 3.9 ) Pub Date : 2020-12-03 , DOI: 10.1002/chem.202004140 Lars E Sattler 1 , Gerhard Hilt 1
Chemistry - A European Journal ( IF 3.9 ) Pub Date : 2020-12-03 , DOI: 10.1002/chem.202004140 Lars E Sattler 1 , Gerhard Hilt 1
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The synthesis of 1,3‐oxazoles from symmetrical and unsymmetrical alkynes was realized by an iodonium cation‐pool electrolysis of I2 in acetonitrile with a well‐defined water content. Mechanistic investigations suggest that the alkyne reacts with the acetonitrile‐stabilized I+ ions, followed by a Ritter‐type reaction of the solvent to a nitrilium ion, which is then attacked by water. The ring closure to the 1,3‐oxazoles released molecular iodine, which was visible by the naked eye. Also, some unsymmetrical internal alkynes were tested and a regioselective formation of a single isomer was determined by two‐dimensional NMR experiments.
中文翻译：
碘阳离子池电解三组分合成1,3-恶唑
由对称和不对称炔烃合成 1,3-恶唑是通过在乙腈中对 I 2进行碘鎓阳离子池电解来实现的，水含量明确。机理研究表明，炔烃与乙腈稳定的 I +离子发生反应，随后溶剂发生 Ritter 型反应，生成腈离子，然后被水攻击。 1,3-恶唑的环闭合释放出肉眼可见的碘分子。此外，还测试了一些不对称的内炔，并通过二维核磁共振实验确定了单一异构体的区域选择性形成。
更新日期：2021-01-07
中文翻译：
碘阳离子池电解三组分合成1,3-恶唑
由对称和不对称炔烃合成 1,3-恶唑是通过在乙腈中对 I 2进行碘鎓阳离子池电解来实现的，水含量明确。机理研究表明，炔烃与乙腈稳定的 I +离子发生反应，随后溶剂发生 Ritter 型反应，生成腈离子，然后被水攻击。 1,3-恶唑的环闭合释放出肉眼可见的碘分子。此外，还测试了一些不对称的内炔，并通过二维核磁共振实验确定了单一异构体的区域选择性形成。
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