钯催化乙烯基恶唑烷-2,4-二酮脱羧丙烯基磺酰化：γ-磺酰-α，β-不饱和酰胺的合成

IF 3.6 2区化学 Q1 CHEMISTRY, ORGANIC

Journal of Organic Chemistry Pub Date : 2025-02-10 DOI:10.1021/acs.joc.4c02743

Wei-Cheng Yuan, Xiao-Hui Fu, Yan-Ping Zhang, Yong You, Jian-Qiang Zhao, Lei Yang, Ming-Qiang Zhou, Zhen-Hua Wang

{"title":"钯催化乙烯基恶唑烷-2,4-二酮脱羧丙烯基磺酰化：γ-磺酰-α，β-不饱和酰胺的合成","authors":"Wei-Cheng Yuan, Xiao-Hui Fu, Yan-Ping Zhang, Yong You, Jian-Qiang Zhao, Lei Yang, Ming-Qiang Zhou, Zhen-Hua Wang","doi":"10.1021/acs.joc.4c02743","DOIUrl":null,"url":null,"abstract":"A palladium-catalyzed decarboxylative allylic sulfonylation reaction of vinyloxazolidine-2,4-diones with inexpensive and readily available sodium sulfinates as sulfonylation reagents has been developed. Under the catalysis of Pd(PPh3)4, a wide range of γ-sulfonyl-α,β-unsaturated amides can be synthesized in good to excellent yields. The developed protocol is characterized by exclusive regioselectivity, mild reaction conditions, broad substrate scope, good functional group tolerance, and suitable for gram-scale synthesis.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"2 1","pages":""},"PeriodicalIF":3.6000,"publicationDate":"2025-02-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Palladium-Catalyzed Decarboxylative Allylic Sulfonylation of Vinyloxazolidine-2,4-diones: Synthesis of γ-Sulfonyl-α,β-unsaturated Amides\",\"authors\":\"Wei-Cheng Yuan, Xiao-Hui Fu, Yan-Ping Zhang, Yong You, Jian-Qiang Zhao, Lei Yang, Ming-Qiang Zhou, Zhen-Hua Wang\",\"doi\":\"10.1021/acs.joc.4c02743\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"A palladium-catalyzed decarboxylative allylic sulfonylation reaction of vinyloxazolidine-2,4-diones with inexpensive and readily available sodium sulfinates as sulfonylation reagents has been developed. Under the catalysis of Pd(PPh3)4, a wide range of γ-sulfonyl-α,β-unsaturated amides can be synthesized in good to excellent yields. The developed protocol is characterized by exclusive regioselectivity, mild reaction conditions, broad substrate scope, good functional group tolerance, and suitable for gram-scale synthesis.\",\"PeriodicalId\":57,\"journal\":{\"name\":\"Journal of Organic Chemistry\",\"volume\":\"2 1\",\"pages\":\"\"},\"PeriodicalIF\":3.6000,\"publicationDate\":\"2025-02-10\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Journal of Organic Chemistry\",\"FirstCategoryId\":\"1\",\"ListUrlMain\":\"https://doi.org/10.1021/acs.joc.4c02743\",\"RegionNum\":2,\"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":"Journal of Organic Chemistry","FirstCategoryId":"1","ListUrlMain":"https://doi.org/10.1021/acs.joc.4c02743","RegionNum":2,"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

以廉价易得的亚硫酸钠为磺化试剂，钯催化乙烯基恶唑烷-2,4-二酮脱羧烯丙基磺化反应。在Pd(PPh3)4的催化下，可以合成多种γ-磺酰-α，β-不饱和酰胺，收率较高。该方案具有区域选择性强、反应条件温和、底物范围广、官能团耐受性好、适合克级合成等特点。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

Palladium-Catalyzed Decarboxylative Allylic Sulfonylation of Vinyloxazolidine-2,4-diones: Synthesis of γ-Sulfonyl-α,β-unsaturated Amides

查看原文本刊更多论文

Palladium-Catalyzed Decarboxylative Allylic Sulfonylation of Vinyloxazolidine-2,4-diones: Synthesis of γ-Sulfonyl-α,β-unsaturated Amides

A palladium-catalyzed decarboxylative allylic sulfonylation reaction of vinyloxazolidine-2,4-diones with inexpensive and readily available sodium sulfinates as sulfonylation reagents has been developed. Under the catalysis of Pd(PPh₃)₄, a wide range of γ-sulfonyl-α,β-unsaturated amides can be synthesized in good to excellent yields. The developed protocol is characterized by exclusive regioselectivity, mild reaction conditions, broad substrate scope, good functional group tolerance, and suitable for gram-scale synthesis.

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

Journal of Organic Chemistry 化学-有机化学

CiteScore

6.20

自引率

11.10%

发文量

1467

审稿时长

2 months

期刊介绍： Journal of Organic Chemistry welcomes original contributions of fundamental research in all branches of the theory and practice of organic chemistry. In selecting manuscripts for publication, the editors place emphasis on the quality and novelty of the work, as well as the breadth of interest to the organic chemistry community.