Rh(I)-催化[4+2]-呋喃-炔烃环丁酮环化及其合成应用

IF 4.7 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Chemistry Frontiers Pub Date : 2025-05-08 DOI:10.1039/D5QO00064E

Lixin Qian, Jingjing Huang, Kemiao Hong, Xinyu Jiang, Mengting Liu, Gang Chen, Dorota Gryko and Xinfang Xu

{"title":"Rh(I)-催化[4+2]-呋喃-炔烃环丁酮环化及其合成应用","authors":"Lixin Qian, Jingjing Huang, Kemiao Hong, Xinyu Jiang, Mengting Liu, Gang Chen, Dorota Gryko and Xinfang Xu","doi":"10.1039/D5QO00064E","DOIUrl":null,"url":null,"abstract":"Fully-substituted aromatic skeletons have received increasing interest from the synthetic chemistry, pharmaceutical and material sciences. However, diversity-oriented construction of these molecules remains challenging due to the lack of effective synthetic building blocks. Herein, we report a Rh(I)-catalyzed [4 + 2]-annulation reaction of alkynes with furan-fused cyclobutanones (FCBs) for the expeditious assembly of fully-substituted o-quinone methide (o-QM) precursors containing a furan-fused motif under mild conditions. These products could be served as practical and robust synthons for the synthesis of fully-substituted phenols with broad functional group compatibility.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":" 18","pages":" 5045-5050"},"PeriodicalIF":4.7000,"publicationDate":"2025-05-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Rh(i)-catalyzed [4 + 2]-annulation of furan-fused cyclobutanones with alkynes and synthetic applications†\",\"authors\":\"Lixin Qian, Jingjing Huang, Kemiao Hong, Xinyu Jiang, Mengting Liu, Gang Chen, Dorota Gryko and Xinfang Xu\",\"doi\":\"10.1039/D5QO00064E\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"Fully-substituted aromatic skeletons have received increasing interest from the synthetic chemistry, pharmaceutical and material sciences. However, diversity-oriented construction of these molecules remains challenging due to the lack of effective synthetic building blocks. Herein, we report a Rh(I)-catalyzed [4 + 2]-annulation reaction of alkynes with furan-fused cyclobutanones (FCBs) for the expeditious assembly of fully-substituted o-quinone methide (o-QM) precursors containing a furan-fused motif under mild conditions. These products could be served as practical and robust synthons for the synthesis of fully-substituted phenols with broad functional group compatibility.\",\"PeriodicalId\":97,\"journal\":{\"name\":\"Organic Chemistry Frontiers\",\"volume\":\" 18\",\"pages\":\" 5045-5050\"},\"PeriodicalIF\":4.7000,\"publicationDate\":\"2025-05-08\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Organic Chemistry Frontiers\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://pubs.rsc.org/en/content/articlelanding/2025/qo/d5qo00064e\",\"RegionNum\":1,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q1\",\"JCRName\":\"CHEMISTRY, ORGANIC\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic Chemistry Frontiers","FirstCategoryId":"92","ListUrlMain":"https://pubs.rsc.org/en/content/articlelanding/2025/qo/d5qo00064e","RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}

引用次数: 0

摘要

全取代芳香骨架在合成化学、制药和材料科学领域受到越来越多的关注。然而，由于缺乏有效的合成构件，这些分子的多样性取向构建仍然具有挑战性。在此，我们报道了Rh(I)催化的[4+2]环烷基与呋喃融合环丁酮（FCBs）的环成环反应，以在温和条件下快速组装含有呋喃融合基序的全取代邻醌甲基（o-QM）前体。这些产物为合成具有广泛官能团相容性的全取代酚类化合物提供了一种实用的合成方法。初步抗肿瘤活性研究表明，化合物3d和5f分别对乳腺癌细胞（MCF-7细胞，IC50 = 1.87±0.33 μM）和结肠癌细胞（HCT-116细胞，IC50 = 1.35±0.15 μM）具有较强的抗肿瘤活性。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

Rh(i)-catalyzed [4 + 2]-annulation of furan-fused cyclobutanones with alkynes and synthetic applications†

查看原文本刊更多论文

Rh(i)-catalyzed [4 + 2]-annulation of furan-fused cyclobutanones with alkynes and synthetic applications†

Fully-substituted aromatic skeletons have received increasing interest from the synthetic chemistry, pharmaceutical and material sciences. However, diversity-oriented construction of these molecules remains challenging due to the lack of effective synthetic building blocks. Herein, we report a Rh(I)-catalyzed [4 + 2]-annulation reaction of alkynes with furan-fused cyclobutanones (FCBs) for the expeditious assembly of fully-substituted o-quinone methide (o-QM) precursors containing a furan-fused motif under mild conditions. These products could be served as practical and robust synthons for the synthesis of fully-substituted phenols with broad functional group compatibility.

求助全文

通过发布文献求助，成功后即可免费获取论文全文。去求助

来源期刊

Organic Chemistry Frontiers CHEMISTRY, ORGANIC-

CiteScore

7.90

自引率

11.10%

发文量

686

审稿时长

1 months

期刊介绍： Organic Chemistry Frontiers is an esteemed journal that publishes high-quality research across the field of organic chemistry. It places a significant emphasis on studies that contribute substantially to the field by introducing new or significantly improved protocols and methodologies. The journal covers a wide array of topics which include, but are not limited to, organic synthesis, the development of synthetic methodologies, catalysis, natural products, functional organic materials, supramolecular and macromolecular chemistry, as well as physical and computational organic chemistry.