Xihong Wang, Yamato Fukuzawa, Pan Gao, Julong Jiang, Satoshi Maeda, Koji Kubota and Hajime Ito
{"title":"用原位机械化学生成的钙基重格氏试剂直接芳基化宝石-二氟苯乙烯","authors":"Xihong Wang, Yamato Fukuzawa, Pan Gao, Julong Jiang, Satoshi Maeda, Koji Kubota and Hajime Ito","doi":"10.1039/D4MR00135D","DOIUrl":null,"url":null,"abstract":"<p >In this study, we disclosed that calcium-based heavy Grignard reagents, prepared <em>in situ</em> through a mechanochemical method, reacted with <em>gem</em>-difluorostyrenes in the absence of transition-metal catalysts to afford thermodynamically less favorable (<em>E</em>)-monofluorostilbenes with good to high stereoselectivity. To the best of our knowledge, this is the first example of nucleophilic substitution of a C(sp<small><sup>2</sup></small>)–F bond by an arylcalcium compound.</p>","PeriodicalId":101140,"journal":{"name":"RSC Mechanochemistry","volume":" 2","pages":" 256-262"},"PeriodicalIF":0.0000,"publicationDate":"2024-12-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://pubs.rsc.org/en/content/articlepdf/2025/mr/d4mr00135d?page=search","citationCount":"0","resultStr":"{\"title\":\"Direct arylation of gem-difluorostyrenes using in situ mechanochemically generated calcium-based heavy Grignard reagents†\",\"authors\":\"Xihong Wang, Yamato Fukuzawa, Pan Gao, Julong Jiang, Satoshi Maeda, Koji Kubota and Hajime Ito\",\"doi\":\"10.1039/D4MR00135D\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<p >In this study, we disclosed that calcium-based heavy Grignard reagents, prepared <em>in situ</em> through a mechanochemical method, reacted with <em>gem</em>-difluorostyrenes in the absence of transition-metal catalysts to afford thermodynamically less favorable (<em>E</em>)-monofluorostilbenes with good to high stereoselectivity. To the best of our knowledge, this is the first example of nucleophilic substitution of a C(sp<small><sup>2</sup></small>)–F bond by an arylcalcium compound.</p>\",\"PeriodicalId\":101140,\"journal\":{\"name\":\"RSC Mechanochemistry\",\"volume\":\" 2\",\"pages\":\" 256-262\"},\"PeriodicalIF\":0.0000,\"publicationDate\":\"2024-12-25\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"https://pubs.rsc.org/en/content/articlepdf/2025/mr/d4mr00135d?page=search\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"RSC Mechanochemistry\",\"FirstCategoryId\":\"1085\",\"ListUrlMain\":\"https://pubs.rsc.org/en/content/articlelanding/2025/mr/d4mr00135d\",\"RegionNum\":0,\"RegionCategory\":null,\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"\",\"JCRName\":\"\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"RSC Mechanochemistry","FirstCategoryId":"1085","ListUrlMain":"https://pubs.rsc.org/en/content/articlelanding/2025/mr/d4mr00135d","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"","JCRName":"","Score":null,"Total":0}
Direct arylation of gem-difluorostyrenes using in situ mechanochemically generated calcium-based heavy Grignard reagents†
In this study, we disclosed that calcium-based heavy Grignard reagents, prepared in situ through a mechanochemical method, reacted with gem-difluorostyrenes in the absence of transition-metal catalysts to afford thermodynamically less favorable (E)-monofluorostilbenes with good to high stereoselectivity. To the best of our knowledge, this is the first example of nucleophilic substitution of a C(sp2)–F bond by an arylcalcium compound.
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