关键词: Paternò–Büchi reaction diaryl ethers oxetanes photochemistry synthetic methods

来  源:   DOI:10.3390/molecules29071513   PDF(Pubmed)

Abstract:
Reported herein is a Paternò-Büchi reaction of aromatic double bonds with quinones under visible light irradiation. The reactions of aromatics with quinones exposed to blue LED irradiation yielded oxetanes at -78 °C, which was attributed to both the activation of double bonds in aromatics and the stabilization of oxetanes by thiadiazole, oxadiazole, or selenadiazole groups. The addition of Cu(OTf)2 to the reaction system at room temperature resulted in the formation of diaryl ethers via the copper-catalyzed ring opening of oxetanes in situ. Notably, the substrate scope was extended to general aromatics.
摘要:
本文报道的是芳族双键与醌在可见光照射下的Paterno²-Büchi反应。芳烃与暴露于蓝光LED辐照的醌的反应在-78°C下产生了氧杂环丁烷,这归因于芳烃中双键的活化和噻二唑对氧杂环丁烷的稳定,恶二唑,或硒二唑基团。在室温下向反应体系中加入Cu(OTf)2导致通过铜催化的氧杂环丁烷原位开环形成二芳基醚。值得注意的是,底物范围扩展到一般芳烃。
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