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光诱导 C-C 键断裂用于从茚酮衍生物和亚磺酰基叶立德合成 2,4-二取代-1-萘酚。

Photoinduced C-C bond cleavage for the synthesis of 2,4-disubstituted-1-naphthols from indenone derivatives and sulfoxonium ylide.

机构信息

Department of Chemistry, Faculty of Science, Mahanakorn University of Technology, 140 Chueam Samphan Rd, Krathum Rai, Nong Chok, Bangkok, 10530, Thailand.

Program on Chemical Sciences, Chulabhorn Graduate Institute, Chulabhorn Royal Academy, Center of Excellence on Environmental Health and Toxicology, CHE, Ministry of Education, 54 Kamphaeng Phet 6, Laksi, Bangkok 10210, Thailand.

出版信息

Org Biomol Chem. 2022 Jul 20;20(28):5520-5524. doi: 10.1039/d2ob00958g.

Abstract

The synthesis of 2,4-disubstituted-1-naphthols has been developed employing photomediated C-C bond cleavage (UV-LED 390 nm) of cyclopropane fused-indanones generated from the reaction between indenones and trimethylsulfoxonium chloride under basic conditions at room temperature. Seventeen substrates were examined in this study. The results showed that indenone precursors containing aryl substituents could smoothly provide the desired products in up to 81% yield.

摘要

本文开发了一种通过光介导的环丙烷稠合茚酮的 C-C 键断裂(UV-LED 390nm)来合成 2,4-二取代-1-萘酚的方法,该方法是通过在碱性条件下室温下将茚酮与三甲基亚砜氯反应生成的。在这项研究中检查了十七个底物。结果表明,含有芳基取代基的茚酮前体可以顺利地以高达 81%的收率提供所需的产物。

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