叔丁醇钾促进的亚胺与芳基卤化物的环化反应

BuOK-Promoted Cyclization of Imines with Aryl Halides.

作者信息

Li Ya-Wei, Zheng Hong-Xing, Yang Bo, Shan Xiang-Huan, Qu Jian-Ping, Kang Yan-Biao

机构信息

Institute of Advanced Synthesis, School of Chemistry and Molecular Engineering, Nanjing Tech University, Nanjing 211816, China.

Department of Chemistry, University of Science and Technology of China, Hefei, Anhui 230026, China.

出版信息

Org Lett. 2020 Jun 5;22(11):4553-4556. doi: 10.1021/acs.orglett.0c01615. Epub 2020 May 21.

DOI:10.1021/acs.orglett.0c01615

PMID:32437166

Abstract

A transition-metal-free indole synthesis using radical coupling of 2-halotoluenes and imines via the later-stage C-N bond construction was reported for the first time. It includes an aminyl radical generation by C-H cleaving addition of 2-halotoluenes to imines via the carbanion radical relay and an intramolecular coupling of aryl halides with aminyl radicals. One standard condition can be used for all halides including F, Cl, Br, and I. No extra oxidant or transition metal is required.

摘要

首次报道了一种通过后期C-N键构建实现2-卤代甲苯与亚胺的自由基偶联的无过渡金属吲哚合成方法。该方法包括通过碳负离子自由基中继将2-卤代甲苯的C-H键裂解加成到亚胺上生成氨基自由基，以及芳基卤化物与氨基自由基的分子内偶联。一种标准条件可用于包括F、Cl、Br和I在内的所有卤化物。无需额外的氧化剂或过渡金属。