Main-group metalated heterocycles through Lewis acid cyclization
Main-group metalated heterocycles through Lewis acid cyclization
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DOI：
10.1016/j.trechm.2021.05.005
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发表时间：
2021-08
影响因子：
15.7
通讯作者：
Chao Gao;S. Blum
中科院分区：
文献类型：
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作者：
Chao Gao;S. Blum
主族金属杂环化合物在合成、药物开发和材料科学中有着广泛的应用。在这篇综述中，我们强调了最近的进展，合成可隔离的主族杂环的硼，铟，硅，锡，硒，碲通过刘易斯酸环化途径和讨论的机制的见解。与传统的先构建杂环再进行金属化的两步合成路线不同，本文所述的刘易斯酸环化反应在一个合成步骤中构建杂环核心并安装金属。这些环化反应以可预测的区域选择性和高官能团耐受性进行。虽然所有描述的反应都是碳-碳π键上的刘易斯酸环化反应，但机理研究表明，不同的金属/试剂可以通过不同的中间体进行。
Main-group metalated heterocycles have broad applications in synthesis, drug development, and materials science. In this review, we highlight recent progress in synthesizing isolable main-group heterocycles of boron, indium, silicon, tin, selenium, and tellurium via Lewis acid cyclization pathways and discuss mechanistic insights. Different from traditional two-step synthetic routes in which heterocycles are constructed first followed by metalation, the herein-described Lewis acid cyclization reactions construct the heterocyclic core and install the metal in one synthetic step. These cyclization reactions proceed with predictable regioselectivity and with high functional group tolerance. While all the described reactions are Lewis acid cyclization reactions onto carbon–carbon π bonds, mechanistic studies show that different metals/reagents can proceed through different intermediates.