Green Tandem [5C + 1C] Cycloaromatization of α‑Alkenoyl Ketene Dithioacetals and Nitroethane in Water: Eco-Friendly Synthesis of Ortho-Acylphenols

For the first time, an eco-friendly and sustainable tandem [5C + 1C] cycloaromatization of α-alkenoyl ketene dithioacetals and nitroethane in water for the efficient synthesis of ortho-acylphenols was reported. In refluxing water, a range of α-alkenoyl ketene dithioacetals and nitroethane smoothly u...

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Published inJournal of organic chemistry Vol. 87; no. 5; pp. 2985 - 2996
Main Authors Yu, Haifeng, Zhang, Zheyu, Zhang, Xue, Xu, Yupeng, Huo, Dongyue, Zhang, Lanyun, Wang, Wenju
Format Journal Article
LanguageEnglish
Published United States American Chemical Society 04.03.2022
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Summary:For the first time, an eco-friendly and sustainable tandem [5C + 1C] cycloaromatization of α-alkenoyl ketene dithioacetals and nitroethane in water for the efficient synthesis of ortho-acylphenols was reported. In refluxing water, a range of α-alkenoyl ketene dithioacetals and nitroethane smoothly underwent tandem Michael addition/cyclization/aromatization reactions in the presence of 2.0 equivalents of DBU to provide various ortho-acylphenols in excellent yields. The green approach to ortho-acylphenols not only avoided the use of harmful organic solvents, which could result in serious environmental and safety issues, but also exhibited fascinating features such as good substrate scope, excellent yields, simple purification for desired products, ease of scale-up, and reusable aqueous medium.
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ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.1c02825