Methanesulfonic Acid‐Catalyzed Friedel‐Crafts Alkylation: Towards Sustainable Synthesis of Arylalkanes from Donor–Acceptor Cyclopropane Ketones

IF 2.8 4区 化学 Q1 CHEMISTRY, ORGANIC Asian Journal of Organic Chemistry Pub Date : 2024-07-01 DOI:10.1002/ajoc.202400116
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Abstract

We present herein Brønsted acid‐catalyzed Friedel‐Crafts alkylation of phenols with Donor–Acceptor cyclopropane ketones. The presence of the 1,4‐diphenyl butan‐1‐one and 1,3‐diphenyl propane‐1‐one motifs in various naturally occurring biologically significant molecules inspired us to pursue the direct synthesis of these structural frameworks. Utilizing methanesulfonic acid (MeSO3H) as a catalyst, we achieved a more environmentally friendly and high‐yielding synthesis, owing to its cost‐effectiveness, biodegradability, transition–metal and additives free conditions. Furthermore, we have successfully extended our developed methodology to thiophenols, resulting in the production of sulfur–based butan‐1‐one derivatives in good yields.

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甲磺酸催化的 Friedel-Crafts 烷基化反应:从供体-受体环丙烷酮实现芳基烷烃的可持续合成
我们在此介绍布氏酸催化的苯酚与供体-受体环丙烷酮的 Friedel-Crafts 烷基化反应。在各种天然生物分子中存在的 1,4-二苯基丁-1-酮和 1,3-二苯基丙-1-酮基团激发了我们追求这些结构框架的直接合成。利用甲磺酸(MeSO3H)作为催化剂,我们实现了一种更环保、更高产的合成方法,这得益于其成本效益、生物降解性、不含过渡金属和添加剂的条件。此外,我们还成功地将所开发的方法扩展到了噻吩酚,从而以良好的产率生产出了硫基丁-1-酮衍生物。
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来源期刊
CiteScore
4.70
自引率
3.70%
发文量
372
期刊介绍: Organic chemistry is the fundamental science that stands at the heart of chemistry, biology, and materials science. Research in these areas is vigorous and truly international, with three major regions making almost equal contributions: America, Europe and Asia. Asia now has its own top international organic chemistry journal—the Asian Journal of Organic Chemistry (AsianJOC) The AsianJOC is designed to be a top-ranked international research journal and publishes primary research as well as critical secondary information from authors across the world. The journal covers organic chemistry in its entirety. Authors and readers come from academia, the chemical industry, and government laboratories.
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