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基于氢原子转移的γ-内酰胺的电化学 C(sp 3 )-H 官能化。

Electrochemical C(sp)-H Functionalization of γ-Lactams Based on Hydrogen Atom Transfer.

机构信息

Department of Chemistry, Ulsan National Institute of Science & Technology (UNIST), Ulsan 44919, Korea.

出版信息

Org Lett. 2022 Jun 17;24(23):4264-4269. doi: 10.1021/acs.orglett.2c01528. Epub 2022 Jun 8.

Abstract

We describe the electrochemical α-amidoalkylation of γ-lactams based on transition-metal-free cross-coupling via hydrogen atom transfer. The highly selective hydrogen atom transfer process allows for a broad substrate scope including both inter- and intramolecular reactions. Also, the construction of quaternary centers was realized by a double hydrogen atom transfer protocol to afford spirocycles. Detailed mechanistic studies including experimental and computational studies are provided to support the reaction pathway.

摘要

我们描述了基于通过氢原子转移的过渡金属自由交叉偶联的γ-内酰胺的电化学α-酰胺烷基化。高度选择性的氢原子转移过程允许广泛的底物范围,包括分子间和分子内反应。此外,通过双氢原子转移协议实现了季碳原子的构建,从而得到螺环化合物。提供了包括实验和计算研究在内的详细的机理研究来支持反应途径。

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