Dihydrobenzofuran production from catalytic tandem Claisen rearrangement–intramolecular hydroaryloxylation of allyl phenyl ethers in subcritical water

We herein report a mild method for the preparation of dihydrobenzofurans through hydrothermal catalytic tandem Claisen rearrangement–intramolecular hydroaryloxylation of allyl phenyl ethers. This reaction provides a new method for constructing dihydrobenzofurans, a process that is potentially applic...

Full description

Saved in:
Bibliographic Details
Published in:RSC advances 2014-01, Vol.4 (56), p.29527-29533
Main Authors: Luo, Ligang, Liu, Chunze, Hou, Zhiqiang, Wang, Yuanyuan, Dai, Liyi
Format: Article
Language:English
Subjects:
Catalysis
Catalysts
Catalytic activity
Construction
Derivatives
Ethers
Phenyls
Synthesis
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:We herein report a mild method for the preparation of dihydrobenzofurans through hydrothermal catalytic tandem Claisen rearrangement–intramolecular hydroaryloxylation of allyl phenyl ethers. This reaction provides a new method for constructing dihydrobenzofurans, a process that is potentially applicable to natural product synthesis. SBA-15, TS-1, HZSM-5 were chosen as catalysts in a hydrothermal reaction medium between 200 and 320 °C. HZSM-5 catalyst showed the highest catalytic activity, and the effects of molar ratio of allyl phenyl ether–water, time, pressure, temperature and catalyst on the Claisen hydroaryloxylation in hydrothermal condition were investigated. The latter two process variables had the greatest influence on the product yields and distribution. A series of allyl phenyl ether derivatives were also treated in hydrothermal condition with HZSM-5 catalyst to offer high yield of corresponding dihydrobenzofurans.
ISSN:2046-2069
2046-2069
DOI:10.1039/C4RA04689G