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电化学合成脱氢 N,C 键形成的 5-芳基-菲啶-6-酮。

Electrochemical Synthesis of 5-Aryl-phenanthridin-6-one by Dehydrogenative N,C Bond Formation.

机构信息

Johannes Gutenberg-Universität Mainz, Institut für Organische Chemie, Duesbergweg 10-14, 55128, Mainz, Germany.

出版信息

Chemistry. 2018 Nov 22;24(65):17230-17233. doi: 10.1002/chem.201804638. Epub 2018 Oct 30.

Abstract

Currently, the general synthesis of 5-aryl-phenanthridin-6-ones relies on the involvement of metal catalysis. Despite the urgent demand for green alternatives, avoiding synthetic routes that require transition metals for key roles is still challenging. Electrochemical efforts employing a constant potential protocol in divided cells revealed a possible alternative to the catalytic approach. A constant current protocol, undivided cells, and a remarkably low supporting electrolyte concentration enable a novel access to N-aryl-phenanthridin-6-ones by anodic N,C bond formation using directly generated amidyl radicals. Easy accessible starting materials, a broad scope of applicable functional groups, good yields, and a very simple set-up are the benefits of this sustainable method.

摘要

目前,5-芳基-菲啶-6-酮的一般合成依赖于金属催化的参与。尽管人们迫切需要绿色替代品,但避免使用需要过渡金属发挥关键作用的合成路线仍然具有挑战性。采用恒电位协议在分隔电池中的电化学研究揭示了一种替代催化方法的可能性。恒电流协议、非分隔电池和非常低的支持电解质浓度使得通过直接生成的酰基自由基的阳极 N,C 键形成来获得 N-芳基-菲啶-6-酮成为可能。这种可持续方法的优点是易于获得的起始材料、广泛的适用官能团、良好的收率和非常简单的设置。

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