Mateos Javier, Vega-Peñaloza Alberto, Franceschi Pietro, Rigodanza Francesco, Andreetta Philip, Companyó Xavier, Pelosi Giorgio, Bonchio Marcella, Dell'Amico Luca
Department of Chemical Sciences, University of Padova Via Marzolo 1 35131 Padova Italy
Department of Chemistry, Life Sciences and Environmental Sustainability, University of Parma Parco Area delle Scienze 17 43124 Parma Italy.
Chem Sci. 2020 Apr 16;11(25):6532-6538. doi: 10.1039/d0sc01569e.
A variety of highly functionalised -containing polycycles (35 examples) are synthesised from simple indoles and aromatic ketones through a mild visible-light Paternò-Büchi process. Tetrahydrooxeto[2,3-]indole scaffolds, with up to three contiguous stereocenters, are generated in high yield (up to >98%) and excellent site- regio- and diastereocontrol (>20 : 1). The use of visible light (405 or 465 nm) ensures enhanced performances by switching off undesired photodimerisation side reactions. The reaction can be easily implemented using a microfluidic photoreactor with improved productivity (up to 0.176 mmol h) and generality. Mechanistic investigations revealed that two alternative reaction mechanisms can account for the excellent regio- and diastereocontrol observed.
通过温和的可见光帕滕诺-布齐反应，由简单的吲哚和芳香酮合成了多种含有高官能团化的多环化合物（35个实例）。生成了具有多达三个相邻立体中心的四氢氧杂环丁烷并[2,3 - ]吲哚支架，产率高（高达>98%），位点、区域和非对映体控制优异（>20 : 1）。使用可见光（405或465 nm）通过关闭不需要的光二聚化副反应确保了性能的提升。该反应可以使用微流控光反应器轻松实现，具有更高的生产率（高达0.176 mmol/h）和通用性。机理研究表明，两种替代反应机制可以解释所观察到的优异区域和非对映体控制。
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