Xiao-Yu Lu , Meng-Ting Gao , Li-Juan Yu , Hong-Ye Pan , Xiang Zhang , Rui Huang , Kang Yang , Fu-Yi Shui , Yi-Wei Song , Gui-Xian Yang
{"title":"通过α-氟丙烯酸和醇的光诱导脱羧交叉偶联合成氟化烯丙醇†","authors":"Xiao-Yu Lu , Meng-Ting Gao , Li-Juan Yu , Hong-Ye Pan , Xiang Zhang , Rui Huang , Kang Yang , Fu-Yi Shui , Yi-Wei Song , Gui-Xian Yang","doi":"10.1039/d3qo00068k","DOIUrl":null,"url":null,"abstract":"<div><p>Herein, a practical and robust methodology for photoinduced decarboxylative and dehydrogenative cross-coupling is reported. A wide range of α-fluoroacrylic acids and structurally diverse alcohols were smoothly converted into the desired fluorinated allylic alcohols with high <em>Z</em>-stereoselectivity under mild conditions. These fluorinated allylic alcohols are versatile building blocks and important structural fragments in organic chemistry and pharmaceutical science. The feasibility of this synthetic strategy was fully demonstrated <em>via</em> a gram-scale reaction, further transformations, and late-stage modifications of bioactive molecules.</p></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"10 7","pages":"Pages 1788-1795"},"PeriodicalIF":0.0000,"publicationDate":"2023-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Synthesis of fluorinated allylic alcohols via photoinduced decarboxylative cross-coupling of α-fluoroacrylic acids and alcohols†\",\"authors\":\"Xiao-Yu Lu , Meng-Ting Gao , Li-Juan Yu , Hong-Ye Pan , Xiang Zhang , Rui Huang , Kang Yang , Fu-Yi Shui , Yi-Wei Song , Gui-Xian Yang\",\"doi\":\"10.1039/d3qo00068k\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><p>Herein, a practical and robust methodology for photoinduced decarboxylative and dehydrogenative cross-coupling is reported. A wide range of α-fluoroacrylic acids and structurally diverse alcohols were smoothly converted into the desired fluorinated allylic alcohols with high <em>Z</em>-stereoselectivity under mild conditions. These fluorinated allylic alcohols are versatile building blocks and important structural fragments in organic chemistry and pharmaceutical science. The feasibility of this synthetic strategy was fully demonstrated <em>via</em> a gram-scale reaction, further transformations, and late-stage modifications of bioactive molecules.</p></div>\",\"PeriodicalId\":94379,\"journal\":{\"name\":\"Organic chemistry frontiers : an international journal of organic chemistry\",\"volume\":\"10 7\",\"pages\":\"Pages 1788-1795\"},\"PeriodicalIF\":0.0000,\"publicationDate\":\"2023-01-01\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Organic chemistry frontiers : an international journal of organic chemistry\",\"FirstCategoryId\":\"1085\",\"ListUrlMain\":\"https://www.sciencedirect.com/org/science/article/pii/S2052411023005916\",\"RegionNum\":0,\"RegionCategory\":null,\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"\",\"JCRName\":\"\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic chemistry frontiers : an international journal of organic chemistry","FirstCategoryId":"1085","ListUrlMain":"https://www.sciencedirect.com/org/science/article/pii/S2052411023005916","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"","JCRName":"","Score":null,"Total":0}
Synthesis of fluorinated allylic alcohols via photoinduced decarboxylative cross-coupling of α-fluoroacrylic acids and alcohols†
Herein, a practical and robust methodology for photoinduced decarboxylative and dehydrogenative cross-coupling is reported. A wide range of α-fluoroacrylic acids and structurally diverse alcohols were smoothly converted into the desired fluorinated allylic alcohols with high Z-stereoselectivity under mild conditions. These fluorinated allylic alcohols are versatile building blocks and important structural fragments in organic chemistry and pharmaceutical science. The feasibility of this synthetic strategy was fully demonstrated via a gram-scale reaction, further transformations, and late-stage modifications of bioactive molecules.