基于接力催化下2-吲哚甲醇的串联反应构建3,3'-双吲哚骨架
Relay catalysis enabled tandem reaction of 2-indolylmethanols for the construction of 3,3'-bisindole skeletons
刘凯悦 1马晓芳 1杨爽 1陈瑜瑜 1徐成晔 1张宇辰 1石枫2
作者信息
- 1. 江苏师范大学化学与材料科学学院,江苏徐州 221116
- 2. 江苏师范大学化学与材料科学学院,江苏徐州 221116;常州大学石油化工学院,江苏常州 213164;河南师范大学化学与化工学院,河南新乡 453007
- 折叠
摘要
发展了一种钯和布朗斯特酸接力催化下2-吲哚甲醇与邻氨基苯乙炔的串联反应,高收率地合成了结构多样的3,3'-双吲哚衍生物(33个样品,产率高达98％).该反应具有较好的实用性,不仅能够放大至克级规模,同时产物还可以进行合成转化.更为重要的是,本文通过控制实验详细研究了接力催化体系中两个催化剂活化底物的模式.该反应为接力催化策略在2-吲哚甲醇参与的串联反应中的应用提供了有益的借鉴,也为合成3,3'-双吲哚衍生物提供了高原子经济性的策略.
Abstract
Herein,we have developed a new strategy for the construction of 3,3'-bisindole skeletons.This strategy makes use of the tandem reaction of 2-indolylmethanols with o-aminophenylacetylenes enabled by the relay catalysis of palladium/Brønsted acid,thus affording structurally diversified 3,3'-bisindoles in generally high yields(33 examples,up to 98％yield).This reaction can be performed in gram scale and the products can undergo synthetic transformation.Moreover,control experiments elucidated the role of the relay catalysis of palladium/Brønsted acid in controlling the reactivity of this tandem reaction.This re-action not only adds a new example to relay catalytic tandem reactions of 2-indolylmethanols,but also pro-vides an atom-economic method for the synthesis of 3,3'-bisindoles.
关键词
3,3'-双吲哚/2-吲哚甲醇/邻氨基苯乙炔/接力催化/串联反应Key words
3,3'-bisindole/2-indolylmethanol/o-aminophenylacetylene/relay catalysis/tandem reaction引用本文复制引用
基金项目
National Natural Science Foundation of China(22125104)
National Natural Science Foundation of China(21831007)
Project for Excellent Scientific and Technological Innovation Team of Jiangsu Province,Undergraduate Students Project of JSNU()
出版年
2024
NETL
NSTL
万方数据