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光氧化还原催化的氨基自由基转移介导的烯烃三组分烷基芳基化反应

Photoredox-Catalyzed Amino-Radical-Transfer-Mediated Three-Component Alkylarylation of Alkenes.

作者信息

Tang Di-Di, Wang Yu-Zhao, Liu Chenjiang, Xia Yu, Li Yan

机构信息

Urumqi Key Laboratory of Green Catalysis and Synthesis Technology, Key Laboratory of Oil and Gas Fine Chemicals, Ministry of Education & Xinjiang Uygur Autonomous Region, State Key Laboratory of Chemistry and Utilization of Carbon Based Energy Resources, College of Chemistry, Xinjiang University, Urumqi 830017, P. R. China.

School of Pharmaceutical Sciences & Institute of Materia Medica, Shandong First Medical University & Shandong Academy of Medical Sciences, Jinan 250117, Shandong, China.

出版信息

Org Lett. 2024 Aug 2;26(30):6477-6481. doi: 10.1021/acs.orglett.4c02335. Epub 2024 Jul 23.

Abstract

We herein reported a novel photoredox-catalyzed three-component alkylarylation of vinyl arenes with alkylboronic pinacol esters (APEs) and cyanoarenes via radical addition/cross-coupling to construct 1,1-diarylalkanes. In this transformation, alkyl radicals were easily available by visible-light-induced oxidative N-H cleavage of morpholine, which used APEs as a radical precursor. Furthermore, this protocol exhibited a broad substrate scope, enabling various styrenes, APEs, and cyanoarenes, as well as bioactive molecule derivatives.

摘要

我们在此报道了一种新型的光氧化还原催化的乙烯基芳烃与烷基硼酸频哪醇酯(APEs)和氰基芳烃的三组分烷基芳基化反应,通过自由基加成/交叉偶联构建1,1-二芳基烷烃。在该转化过程中,通过可见光诱导的吗啉的氧化N-H裂解可轻松获得烷基自由基,该反应使用APEs作为自由基前体。此外,该方案具有广泛的底物范围,适用于各种苯乙烯、APEs和氰基芳烃以及生物活性分子衍生物。

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