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

作者：Luo, Ligang; Liu, Chunze; Hou, Zhiqiang; Wang, Yuanyuan^*; Dai, Liyi

来源：RSC Advances, 2014, 4(56): 29527-29533.

DOI：10.1039/c4ra04689g

• Allyl phenyl ether
• Claisen rearrangement
• Dihydrobenzofurans
• Hydrothermal conditions
• Hydrothermal reaction
• Natural product synthesis
• Process Variables
• Sub-critical 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 applicable to natural product synthesis. SBA-15, TS-1, HZSM-5 were chosen as catalysts in a hydrothermal reaction medium between 200 and 320 degrees 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.

• 出版日期2014
• 单位华东师范大学