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溴代硝基烷烃通过可见光照光氧化还原催化引发 α,α-二芳基烯丙基醇 TMS 醚的自由基 1,2-芳基迁移。

-Bromonitroalkane Involved Radical 1,2-Aryl Migration of α,α-Diaryl Allyl Alcohol TMS Ether via Visible-Light Photoredox Catalysis.

机构信息

College of Chemistry, Beijing Normal University, Beijing 100875, P. R. China.

出版信息

J Org Chem. 2023 Apr 7;88(7):4743-4756. doi: 10.1021/acs.joc.3c00343. Epub 2023 Mar 27.

Abstract

A mild and efficient coupling method concerning the reactions of -bromonitroalkanes with α,α-diaryl allyl alcohol trimethylsilyl ethers was reported. A cascade consisting of visible-light-induced generation of an α-nitroalkyl radical and a subsequent neophyl-type rearrangement was key to realize the coupling reactions. Structurally diverse α-aryl-γ-nitro ketones, especially those bearing a nitrocyclobutyl structure, were prepared in moderate to high yields, which could be converted into spirocyclic nitrones and imines.

摘要

本文报道了一种温和高效的 -溴代硝基烷与α,α-二芳基烯丙基醇三甲基硅醚反应的偶联方法。可见光诱导生成α-硝基烷基自由基和随后的新戊型重排反应的级联反应是实现偶联反应的关键。合成了结构多样的α-芳基-γ-硝基酮,特别是那些含有硝基环丁基结构的化合物,产率中等至较高,这些产物可进一步转化为螺环硝酮和亚胺。

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