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Iodide Ion-Promoted Highly Regioselective Triazolization of Aldehydes via Desulfonation-Associated Direct Radical Coupling
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2024-11-11 , DOI: 10.1021/acs.joc.4c01577
Yaqi Deng, Qinghua Wei, Jian Xue, Xiang Wu, Shunying Liu

A highly efficient iodide ion (I)-promoted method for direct α-C(sp2)–H triazolization of aldehydes has been developed for the regioselective synthesis of N2-substituted triazole derivatives. The developed method features the corresponding products in good yields (up to 99%) with an excellent functional group tolerance via an intermolecular oxidative radical coupling. Experimental mechanistic investigations indicate that the reaction proceeds via an I-promoted synergistic desulfonylation process, which provides a high regioselectivity. The developed method provides a direct, metal-free, operationally simple, and highly regioselective approach to C(sp2)–H triazolization from easily accessible aldehydes in air.

中文翻译:


碘离子促进的醛类高区域选择性三唑化,通过脱磺化相关的直接自由基偶联



已经开发了一种用于醛的直接 α-C(sp2)–H 三唑化的高效碘离子 (I) 促进方法,用于 N2-取代的三唑衍生物的区域选择性合成。开发的方法通过分子间氧化自由基偶联获得相应的产物,产率高(高达 99%),具有出色的官能团耐受性。实验机理研究表明,反应通过 I 促进的协同脱磺酰化过程进行,该过程提供了高区域选择性。开发的方法提供了一种直接、无金属、操作简单且高度区域选择性的方法,可从空气中易于接近的醛中进行 C(sp2)-H 三唑化反应。
更新日期:2024-11-12
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