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α-芳基丙烯酰胺与未活化的烷基和芳基氯的氧化还原中性自由基串联环化反应

Redox-Neutral Radical Cascade Cyclization of -Arylacrylamides with Unactivated Alkyl and Aryl Chlorides.

作者信息

Jha Avishek Kumar, Nair Dhananjay P, Arif Munaifa, Yedase Girish Suresh, Kuniyil Rositha, Yatham Veera Reddy

机构信息

School of Chemistry, Indian Institute of Science Education and Research, Thiruvananthapuram 695551, India.

Department of Chemistry, Indian Institute of Technology Palakkad, Palakkad 678623, India.

出版信息

J Org Chem. 2023 Nov 3;88(21):15389-15394. doi: 10.1021/acs.joc.3c01904. Epub 2023 Oct 24.

Abstract

Herein, we report the first metal-free, redox-neutral strategy for radical cascade alkylative radical addition, cyclization of -arylacrylamides with unactivated alkyl chlorides to give corresponding 3,3-disubstituted oxindoles in moderate to good yields. This transformation's salient features are the utilization of an organo photocatalyst, mild reaction conditions, and broad substrate scope. Moreover, this methodology is suitable for hetero cycle derived acrylamides and further allowed to utilize aryl chlorides for radical cyclization reaction. Finally, DFT studies allow us to shed light on the reaction mechanism.

摘要

在此,我们报道了首例无金属、氧化还原中性的自由基串联烷基化自由基加成反应,即芳基丙烯酰胺与未活化的烷基氯进行环化反应,以中等至良好的产率得到相应的3,3-二取代氧化吲哚。该转化反应的显著特点是使用了有机光催化剂、温和的反应条件以及广泛的底物范围。此外,该方法适用于杂环衍生的丙烯酰胺,并且还能进一步用于芳基氯的自由基环化反应。最后,密度泛函理论(DFT)研究使我们能够深入了解反应机理。

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