Fragment Coupling Reactions in Total Synthesis That Form Carbon-Carbon Bonds via Carbanionic or Free Radical Intermediates.,Angewandte Chemie International Edition

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Fragment Coupling Reactions in Total Synthesis That Form Carbon-Carbon Bonds via Carbanionic or Free Radical Intermediates.
Angewandte Chemie International Edition ( IF 16.1 ) Pub Date : 2019-12-23 , DOI: 10.1002/anie.201913645
Martin Tomanik ₁ , Ian Tingyung Hsu ₁ , Seth B Herzon _{1,

2}

Affiliation

Fragment coupling reactions that form carbon–carbon bonds are valuable transformations in synthetic design. Advances in metal‐catalyzed cross‐coupling reactions in the early 2000s brought a high level of predictability and reliability to carbon–carbon bond constructions involving the union of unsaturated fragments. By comparison, recent years have witnessed an increase in fragment couplings proceeding via carbanionic and open‐shell (free radical) intermediates. The latter has been driven by advances in methods to generate and utilize carbon‐centered radicals under mild conditions. In this Review, we survey a selection of recent syntheses that have implemented carbanion‐ or radical‐based fragment couplings to form carbon–carbon bonds. We aim to highlight the strategic value of these disconnections in their respective settings and to identify extensible lessons from each example that might be instructive to students.

中文翻译：

通过碳负离子或自由基中间体形成碳-碳键的全合成中的片段偶联反应。

形成碳-碳键的片段偶联反应是合成设计中有价值的转变。2000年代初，金属催化的交叉偶联反应的进展为涉及不饱和碎片结合的碳-碳键结构带来了很高的可预测性和可靠性。相比之下，近年来见证了通过碳负离子和开壳（自由基）中间体进行的片段偶联的增加。后者是由在温和条件下产生和利用以碳为中心的自由基的方法的进步所驱动的。在本综述中，我们调查了一些最近的合成，这些合成已实现了基于碳负离子或自由基的片段偶联，以形成碳-碳键。

更新日期：2019-12-23

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