通过嬗变获得 N-杂环戊烯

IF 42.8 1区 化学 Q1 CHEMISTRY, PHYSICAL Nature Catalysis Pub Date : 2024-05-29 DOI:10.1038/s41929-024-01174-9
Jan-Stefan Völler
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引用次数: 0

摘要

现在,Peng-Fei Xu、Hao Wei 及其同事报告了一种一锅式扩环-缩合序列,该序列能够在壬醇中实现碳-氮嬗变,生成 N-杂环戊烯(如图)。研究人员首先使用甲基菲-9-醇作为模型底物,并使用二苯基磷酸酯、N-溴代琥珀酰亚胺和四丁基氮化铵作为试剂,生成叠氮酮中间体 I。铁盐的存在对于催化随后的扩环过程非常重要,扩环过程中会形成一种金属-烯,这种烯会发生分子内 1,2-芳基迁移,生成中间体 II。此外,铁催化剂还参与了随后的环收缩。后者包括中间体 III 的开环步骤,中间体 III 经过环化和脱水,得到 N-teroarene 产物。使用三环己基氧化膦作为配体提高了反应产率。以钌、铜、钴和铑为基础的催化剂在进行这种转化时效果较差。在确定了最佳反应条件后,研究人员对底物范围进行了探索,发现萘酚、菲醇、蒽醇、苯并(a)蒽醇、苯并[c]菲醇和融合杂环戊醇等多种多环化合物均可与该反应相容。通过将环系统中的一个碳原子换成一个氮原子,可以直接获得在许多具有生物活性的化合物中普遍存在的含氮杂环基团,为从头合成由此产生的复杂多环化合物提供了一种替代方法。这种合成方法还可用于研究药物化学中的结构-活性关系。
本文章由计算机程序翻译,如有差异,请以英文原文为准。

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N-heteroarenes via transmutation
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来源期刊
Nature Catalysis
Nature Catalysis Chemical Engineering-Bioengineering
CiteScore
52.10
自引率
1.10%
发文量
140
期刊介绍: Nature Catalysis serves as a platform for researchers across chemistry and related fields, focusing on homogeneous catalysis, heterogeneous catalysis, and biocatalysts, encompassing both fundamental and applied studies. With a particular emphasis on advancing sustainable industries and processes, the journal provides comprehensive coverage of catalysis research, appealing to scientists, engineers, and researchers in academia and industry. Maintaining the high standards of the Nature brand, Nature Catalysis boasts a dedicated team of professional editors, rigorous peer-review processes, and swift publication times, ensuring editorial independence and quality. The journal publishes work spanning heterogeneous catalysis, homogeneous catalysis, and biocatalysis, covering areas such as catalytic synthesis, mechanisms, characterization, computational studies, nanoparticle catalysis, electrocatalysis, photocatalysis, environmental catalysis, asymmetric catalysis, and various forms of organocatalysis.
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