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N-溴代丁二酰亚胺诱导的 C-H 键功能化:吸电子取代的 1-联苯-2-基乙酮的分子内环化反应合成 10-菲醇。

N-Bromosuccinimide-Induced C-H Bond Functionalization: An Intramolecular Cycloaromatization of Electron Withdrawing Group Substituted 1-Biphenyl-2-ylethanone for the Synthesis of 10-Phenanthrenol.

机构信息

State Key Laboratory of Medicinal Chemical Biology, College of Pharmacy and Tianjin Key Laboratory of Molecular Drug Research , Nankai University , Haihe Education Park, 38 Tongyan Road , Tianjin 300353 , People's Republic of China.

出版信息

Org Lett. 2018 Jul 6;20(13):3728-3731. doi: 10.1021/acs.orglett.8b01160. Epub 2018 Jun 20.

Abstract

An NBS-induced intramolecular cycloaromatization for the synthesis of 10-phenanthrenols from electron-withdrawing group substituted 1-biphenyl-2-ylethanones is described. The in situ generated bromide was designed to act as an initiator for the radical C-H bond activation. An oxidative cross-dehydrogenative coupling reaction of a highly active C-H bond with an inert C-H bond readily occurs under mild conditions without the need for transition metals or strong oxidants.

摘要

本文描述了一种 NBS 诱导的分子内环化反应,用于从取代的 1-联苯-2-基乙酮合成 10-菲醇。设计了原位生成的溴化物作为自由基 C-H 键活化的引发剂。在温和条件下,无需过渡金属或强氧化剂,高度活性的 C-H 键与惰性 C-H 键之间的氧化交叉脱氢偶联反应很容易发生。

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