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光诱导电子给体-受体(EDA)配合物实现未活化烯烃与2-氨基-1,4-萘醌的自由基串联环化/芳基化反应

Photoinduced EDA Complexes Enabled Radical Tandem Cyclization/Arylation of Unactivated Alkene with 2-Amino-1,4-naphthoquinones.

作者信息

Sun Bin, Shi Xiayue, Zhuang Xiaohui, Huang Panyi, Shi Rongcheng, Zhu Rui, Jin Can

机构信息

Collaborative Innovation Center of Yangtze River Delta Region Green Pharmaceuticals, Zhejiang University of Technology, Hangzhou 310014, P. R. China.

College of Pharmaceutical Sciences, Zhejiang University of Technology, Hangzhou 310014, P. R. China.

出版信息

Org Lett. 2021 Mar 5;23(5):1862-1867. doi: 10.1021/acs.orglett.1c00268. Epub 2021 Feb 19.

Abstract

A visible-light-induced radical tandem cyclization/arylation between 2-amino-1, 4-naphthoquinone and -allyl-2-bromo-2,2-difluoroacetamides has been developed without an external photocatalyst. The transformation could be carried out at room temperature and gave a variety of C-3-functionalized 2-amino-1,4-naphthoquinone derivatives in moderate to excellent yields. Moreover, mechanistic studies revealed that the reaction is driven by the formation of an electron donor-acceptor (EDA) complex.

摘要

已开发出一种在无外部光催化剂的情况下,2-氨基-1,4-萘醌与烯丙基-2-溴-2,2-二氟乙酰胺之间的可见光诱导自由基串联环化/芳基化反应。该转化反应可在室温下进行,能以中等至优异的产率得到多种C-3官能化的2-氨基-1,4-萘醌衍生物。此外,机理研究表明该反应是由电子给体-受体(EDA)络合物的形成驱动的。

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