1,3-Dibromo-5,5-dimethylhydantoin (DBH)/DMSO mediated oxidative difunctionalization of styrenes: Microfluidic synthesis of pentafluorophenoxy ketone

[Display omitted] •A DBH/DMSO oxidative system combined with continuous flow reactor is developed.•This reaction features simple starting materials and a broad substrate scope.•Based on various control experiments, a reasonable mechanism is proposed.•A scale-up reaction is successfully conducted. A...

Full description

Saved in:
Bibliographic Details
Published in:Tetrahedron letters 2021-03, Vol.67, p.152876, Article 152876
Main Authors: Xu, Jia, Hua, Jiawei, Bian, Mixue, Li, Yuguang, He, Wei, Yang, Zhao, Liu, Chengkou, Fang, Zheng, Guo, Kai
Format: Article
Language:English
Subjects:
Continuous flow system
DBH/DMSO
Metal-free
Pentafluorophenoxy ketone
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:[Display omitted] •A DBH/DMSO oxidative system combined with continuous flow reactor is developed.•This reaction features simple starting materials and a broad substrate scope.•Based on various control experiments, a reasonable mechanism is proposed.•A scale-up reaction is successfully conducted. A practical and mild synthesis of pentafluorophenoxy ketone in a continuous flow microfluidic reactor has been developed through 1,3-Dibromo-5,5-dimethylhydantoin (DBH)/DMSO mediated oxidative coupling of styrenes with pentafluorophenol. Moreover, a series of pentafluorophenoxy ketone products were provided in moderate to good yields under metal-free conditions. A magnifying continuous flow system was erected to verify the appliance of this method.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2021.152876