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Pd-catalyzed three-component [2 + 2 + 1] cycloamination toward carbazoles
Organic & Biomolecular Chemistry ( IF 3.2 ) Pub Date : 2024-03-29 , DOI: 10.1039/d4ob00356j
Mingzhu Shen 1 , Min Li 1 , Jingxun Yu 1
Affiliation  

Conventional approaches using hydroxylamine derivatives as single nitrogen sources for the preparation of N-heterocyclic molecules rely on two chemical processes involving sequential nucleophilic and electrophilic C–N bond formations. Herein, we report a novel Suzuki reaction/C–H activation/amination sequence for building a myriad of carbazoles in a single transformation using bifunctional secondary hydroxylamines. It is noteworthy that the synthetic utility of this methodology is highlighted by the total synthesis of clausine V and glycoborine by incorporating the title [2 + 2 + 1] cycloamination as the key step. Control experiments were performed to gain a better understanding of the reaction mechanism.

中文翻译:

Pd催化三组分[2 + 2 + 1]环胺化生成咔唑

使用羟胺衍生物作为单一氮源来制备 N-杂环分子的传统方法依赖于涉及连续亲核和亲电 C-N 键形成的两个化学过程。在此,我们报告了一种新颖的铃木反应/C-H活化/胺化序列,用于使用双功能仲羟胺在一次转化中构建无数咔唑。值得注意的是,通过将标题[2 + 2 + 1]环胺化作为关键步骤,克劳辛V和糖硼烷的全合成突出了该方法的合成效用。进行对照实验以更好地了解反应机理。
更新日期:2024-03-29
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