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有机光氧化还原催化的分子间氧杂-[4+2]环加成反应

Organophotoredox-Catalyzed Intermolecular Oxa-[4+2] Cycloaddition Reactions.

作者信息

Tanaka Kenta, Omata Daichi, Asada Yosuke, Hoshino Yujiro, Honda Kiyoshi

机构信息

Graduate School of Environment and Information Sciences , Yokohama National University , Tokiwadai , Hodogaya-ku, Yokohama 240-8501 , Japan.

出版信息

J Org Chem. 2019 Sep 6;84(17):10669-10678. doi: 10.1021/acs.joc.9b01156. Epub 2019 Aug 1.

Abstract

An intermolecular oxa-[4+2] cycloaddition reaction promoted by a thioxanthylium photoredox catalyst under irradiation with green light has been developed. The reaction of -quinone methides with styrenes smoothly affords the desired cycloadducts. Especially styrenes bearing electron-donating groups are efficiently transformed in this reaction. This method represents a sustainable way to carry out oxa-[4+2] cycloaddition reactions using only a catalytic amount of a photocatalyst and visible light.

摘要

已开发出一种在绿光照射下由硫代呫吨光氧化还原催化剂促进的分子间氧杂-[4+2]环加成反应。醌甲基化物与苯乙烯的反应顺利得到所需的环加合物。特别是带有供电子基团的苯乙烯在该反应中能有效地转化。该方法代表了一种仅使用催化量的光催化剂和可见光进行氧杂-[4+2]环加成反应的可持续方式。

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