Synthesis of Benzoxazoles Using Electrochemically Generated Hypervalent Iodine,The Journal of Organic Chemistry

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Synthesis of Benzoxazoles Using Electrochemically Generated Hypervalent Iodine
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2017-08-25 00:00:00 , DOI: 10.1021/acs.joc.7b01686
Olesja Koleda ₁ , Timo Broese ₂ , Jan Noetzel ₃ , Michael Roemelt _{3,

4} , Edgars Suna ₁ , Robert Francke ₂

Affiliation

The indirect (“ex-cell”) electrochemical synthesis of benzoxazoles from imines using a redox mediator based on the iodine(I)/iodine(III) redox couple is reported. Tethering the redox-active iodophenyl subunit to a tetra-alkylammonium moiety allowed for anodic oxidation to be performed without supporting electrolyte. The mediator salt can be easily recovered and reused. Our “ex-cell” approach toward the electrosynthesis of benzoxazoles is compatible with a range of redox-sensitive functional groups. An unprecedented concerted reductive elimination mechanism for benzoxazole formation is proposed on the basis of control experiments and DFT calculations.

中文翻译：

电化学生成的高价碘合成苯并恶唑

据报道，使用基于碘（I）/碘（III）氧化还原对的氧化还原介体从亚胺间接（“细胞外”）电化学合成苯并恶唑。将氧化还原活性的碘代苯基亚基束缚到四烷基铵部分上，从而可以在不支持电解质的情况下进行阳极氧化。介体盐可以很容易地回收和再利用。我们对苯并恶唑进行电合成的“细胞外”方法与一系列对氧化还原敏感的官能团兼容。在控制实验和DFT计算的基础上，提出了前所未有的协同消除苯并恶唑形成的机理。

更新日期：2017-08-25

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