{"title":"(2-甲基-3-氧代异吲哚啉-1-基)三苯基膦四氟硼酸盐的合成和 Wittig 烯化反应：3-亚烷基-2-甲基异吲哚啉-1-酮的简便获取途径","authors":"Wenhua Huang , Yan-Hong Wang","doi":"10.1080/10426507.2023.2263131","DOIUrl":null,"url":null,"abstract":"<div><p>(2-Methyl-3-oxoisoindolin-1-yl)triphenylphosphonium tetrafluoroborate has been successfully synthesized from Ph<sub>3</sub>PHBF<sub>4</sub> and 3-hydroxy-2-methylisoindolin-1-one. It undergoes smoothly Wittig olefination with a variety of aldehydes when using DBU or <em>t</em>-BuOK as a base to furnish 3-(alkylidene)-2-methyisoindolin-1-ones in 35–93% yields with the stereoselectivity being mostly favorable to (<em>E</em>)-isomer.</p></div>","PeriodicalId":20056,"journal":{"name":"Phosphorus, Sulfur, and Silicon and the Related Elements","volume":"199 1","pages":"Pages 82-89"},"PeriodicalIF":1.4000,"publicationDate":"2024-01-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Synthesis and Wittig olefination of (2-methyl-3-oxoisoindolin-1-yl)triphenylphosphonium tetrafluoroborate: facile access to 3-alkylidene-2-methylisoindolin-1-ones\",\"authors\":\"Wenhua Huang , Yan-Hong Wang\",\"doi\":\"10.1080/10426507.2023.2263131\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><p>(2-Methyl-3-oxoisoindolin-1-yl)triphenylphosphonium tetrafluoroborate has been successfully synthesized from Ph<sub>3</sub>PHBF<sub>4</sub> and 3-hydroxy-2-methylisoindolin-1-one. It undergoes smoothly Wittig olefination with a variety of aldehydes when using DBU or <em>t</em>-BuOK as a base to furnish 3-(alkylidene)-2-methyisoindolin-1-ones in 35–93% yields with the stereoselectivity being mostly favorable to (<em>E</em>)-isomer.</p></div>\",\"PeriodicalId\":20056,\"journal\":{\"name\":\"Phosphorus, Sulfur, and Silicon and the Related Elements\",\"volume\":\"199 1\",\"pages\":\"Pages 82-89\"},\"PeriodicalIF\":1.4000,\"publicationDate\":\"2024-01-02\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Phosphorus, Sulfur, and Silicon and the Related Elements\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://www.sciencedirect.com/org/science/article/pii/S1042650723002332\",\"RegionNum\":4,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q4\",\"JCRName\":\"CHEMISTRY, INORGANIC & NUCLEAR\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Phosphorus, Sulfur, and Silicon and the Related Elements","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/org/science/article/pii/S1042650723002332","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q4","JCRName":"CHEMISTRY, INORGANIC & NUCLEAR","Score":null,"Total":0}
Synthesis and Wittig olefination of (2-methyl-3-oxoisoindolin-1-yl)triphenylphosphonium tetrafluoroborate: facile access to 3-alkylidene-2-methylisoindolin-1-ones
(2-Methyl-3-oxoisoindolin-1-yl)triphenylphosphonium tetrafluoroborate has been successfully synthesized from Ph3PHBF4 and 3-hydroxy-2-methylisoindolin-1-one. It undergoes smoothly Wittig olefination with a variety of aldehydes when using DBU or t-BuOK as a base to furnish 3-(alkylidene)-2-methyisoindolin-1-ones in 35–93% yields with the stereoselectivity being mostly favorable to (E)-isomer.
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Phosphorus, Sulfur, and Silicon and the Related Elements is a monthly publication intended to disseminate current trends and novel methods to those working in the broad and interdisciplinary field of heteroatom chemistry.
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