3,4,5-Trimethylphenol and Lewis Acid Dual-Catalyzed Cascade Ring-Opening/Cyclization: Direct Synthesis of Naphthalenes,Organic Letters

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3,4,5-Trimethylphenol and Lewis Acid Dual-Catalyzed Cascade Ring-Opening/Cyclization: Direct Synthesis of Naphthalenes
Organic Letters ( IF 4.9 ) Pub Date : 2017-12-01 00:00:00 , DOI: 10.1021/acs.orglett.7b03392
He Ma ₁ , Xiu-Qin Hu ₁ , Yong-Chun Luo ₁ , Peng-Fei Xu ₁

Affiliation

A 3,4,5-trimethylphenol and Lewis acid dual-catalyzed cascade reaction of donor–acceptor (D–A) cyclopropanes via ring-opening and cyclization is developed. In this reaction, a phenolic compound was used as a covalent catalyst for the first time. Additionally, control experiments proved that 3,4,5-trimethylphenol completed the catalytic cycle by accomplishing the C–C bond cleavage. Using this strategy, a wide variety of substituted naphthalenes has been synthesized from D–A cyclopropanes in moderate to high yields under mild conditions.

中文翻译：

3,4,5-三甲基苯酚和路易斯酸双催化级联开环/环化反应：萘的直接合成

通过开环和环化反应，开发了一种3,4,5-三甲基苯酚和路易斯酸双重催化的供体-受体（DA）环丙烷级联反应。在该反应中，酚类化合物首次被用作共价催化剂。另外，对照实验证明3,4,5-三甲基苯酚通过完成C–C键断裂而完成了催化循环。使用这种策略，在温和条件下，由D–A环丙烷以中等到高收率合成了各种各样的取代萘。

更新日期：2017-12-01

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