胺气处理
硝基苯
硝基
化学
卤化
组合化学
戒指(化学)
分子
立体化学
有机化学
催化作用
烷基
作者
Raquel Sánchez-Bento,Baptiste Roure,Josep Llaveria,Alessandro Ruffoni,Daniele Leonori
出处
期刊:Chem
[Elsevier]
日期:2023-12-01
卷期号:9 (12): 3685-3695
被引量:3
标识
DOI:10.1016/j.chempr.2023.10.008
摘要
Ortho-phenylenediamines are aromatic molecules featuring two vicinal N-substituents with strong structural relevance to the development of bioactive materials. These derivatives are currently prepared from ortho-halogenated nitrobenzenes via multistep synthetic sequences. Here, we report a conceptually different approach where nitrobenzenes and amines can be directly converted into ortho-phenylenediamines without the need for ortho-halogenation and following stepwise synthetic manipulation. This strategy occurs under simple blue light irradiation and introduces an alternative retrosynthetic tactic whereby the amine coupling partner “seems” to displace the nitro group that shifts to its ortho position while being reduced and amidated in a one-pot process. Mechanistically, this process capitalizes on the conversion of nitrobenzenes into the corresponding single nitrenes, which undergo a series of N-insertion, electrocyclic ring expansion, amine addition, and electrocyclic ring contraction en route to the ortho-phenylenediamines.
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