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

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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Veröffentlicht in:Journal of organic chemistry 2022-03, Vol.87 (5), p.2985-2996
Hauptverfasser: Yu, Haifeng, Zhang, Zheyu, Zhang, Xue, Xu, Yupeng, Huo, Dongyue, Zhang, Lanyun, Wang, Wenju
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container_end_page 2996
container_issue 5
container_start_page 2985
container_title Journal of organic chemistry
container_volume 87
creator Yu, Haifeng
Zhang, Zheyu
Zhang, Xue
Xu, Yupeng
Huo, Dongyue
Zhang, Lanyun
Wang, Wenju
description 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.
doi_str_mv 10.1021/acs.joc.1c02825
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title Green Tandem [5C + 1C] Cycloaromatization of α‑Alkenoyl Ketene Dithioacetals and Nitroethane in Water: Eco-Friendly Synthesis of Ortho-Acylphenols
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