Li Xinwei, Cheng Zengrui, Liu Jianzhong, Zhang Ziyao, Song Song, Jiao Ning
State Key Laboratory of Natural and Biomimetic Drugs, Chemical Biology Center, School of Pharmaceutical Sciences, Peking University Xue Yuan Rd. 38 Beijing 100191 China
Shanghai Key Laboratory of Green Chemistry and Chemical Processes, East China Normal University Shanghai 200062 China.
Chem Sci. 2022 Jul 6;13(31):9056-9061. doi: 10.1039/d2sc02210a. eCollection 2022 Aug 10.
C(sp)-H bond desaturation has been an attractive strategy in organic synthesis. Enamides are important structural fragments in pharmaceuticals and versatile synthons in organic synthesis. However, the dehydrogenation of amides usually occurs on the acyl side benefitting from enolate chemistry like the desaturation of ketones and esters. Herein, we demonstrate an Fe-assisted regioselective oxidative desaturation of amides, which provides an efficient approach to enamides and β-halogenated enamides.
C(sp) -H键去饱和反应一直是有机合成中一种具有吸引力的策略。烯酰胺是药物中的重要结构片段以及有机合成中的通用合成子。然而，酰胺的脱氢反应通常发生在酰基一侧，这得益于烯醇盐化学，类似于酮和酯的去饱和反应。在此，我们展示了一种铁辅助的酰胺区域选择性氧化去饱和反应，该反应为烯酰胺和β-卤代烯酰胺提供了一种有效的合成方法。
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