Computational design of an intramolecular photocyclization reaction with state-selective reactivity: a strategy for indole synthesis
Computational design of an intramolecular photocyclization reaction with state-selective reactivity: a strategy for indole synthesis
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具有状态选择性反应性的分子内光环化反应的计算设计：吲哚合成策略
DOI：
10.1039/c9gc02676b
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发表时间：
2019
期刊：
影响因子：
9.8
通讯作者：
Wei Wentao
中科院分区：
文献类型：
--
作者：
Zhou Jingwei;Li Lamei;Yan Ming;Wei Wentao
开发一种方便、环境友好的吲哚合成方法具有重要的方法学和药学意义。在这项工作中，我们发现了一个不依赖于光催化剂的羰基化合物和叔胺的吲哚合成的分子内环化。在温和的反应条件下，以中等至优异的产率制备了多种功能性吲哚。此外，我们广泛的量子力学（QM）计算和合成实验揭示了这种反应的“状态选择性反应性”的特点，不同的底物类型可以通过这种功能实现不同的产率。这种新的见解之间的相互作用的“状态选择性反应性”和产量强调其重要性，并提供指导有关的“状态选择性反应性”的高产率的各种吲哚衍生物。
The development of a convenient and environmentally friendly indole synthesis method is of great methodological and pharmaceutical interest. In this work, we discovered an intramolecular photocyclization of carbonyls and tertiary amines for indole synthesis without relying on photocatalysts. A wide range of functional indoles were prepared with moderate to excellent yields under mild reaction conditions. Furthermore, our extensive quantum mechanics (QM) calculations and synthesis experiments revealed the ‘state-selective reactivity’ feature of this reaction, and different substrate types can achieve different yields through this feature. This new insight into the interplay between the ‘state-selective reactivity’ and the yields emphasizes its importance and gives guidance regarding the ‘state-selective reactivity’ for the high yield of various indole derivatives.