Xun Yang , Yuxuan Xiao , Ying Yin , Haiyan Li , Jiahui Du , Xin Li , Wengui Duan , Lin Yu
{"title":"可见光或日光光氧化还原催化烯烃β选择性酰化以获得α, β-不饱和酮","authors":"Xun Yang , Yuxuan Xiao , Ying Yin , Haiyan Li , Jiahui Du , Xin Li , Wengui Duan , Lin Yu","doi":"10.1039/d4qo02101k","DOIUrl":null,"url":null,"abstract":"<div><div>With increasing concerns regarding the energy crisis and environmental changes, the development of sunlight-based methods for organic synthesis has become imperative. We present a masking enone strategy that effectively suppresses side reactions associated with enone products, enabling the β-selective acylation of alkenes catalyzed by excited-state copper under sunlight or visible light. This reaction yields highly valuable α,β-unsaturated ketones, which can be readily transformed into important building blocks through various conversions. Notably, this method is characterized by its sustainable and eco-friendly energy source, mild reaction conditions, high compatibility with functional groups, and suitability for gram-scale synthesis, making it promising for late-stage modifications of complex molecules. Mechanistic studies indicate that the reaction proceeds via a free radical pathway.</div></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"12 5","pages":"Pages 1543-1549"},"PeriodicalIF":0.0000,"publicationDate":"2025-01-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Visible-light or sunlight photoredox-catalyzed β-selective acylation of alkenes to access α,β-unsaturated ketones†\",\"authors\":\"Xun Yang , Yuxuan Xiao , Ying Yin , Haiyan Li , Jiahui Du , Xin Li , Wengui Duan , Lin Yu\",\"doi\":\"10.1039/d4qo02101k\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><div>With increasing concerns regarding the energy crisis and environmental changes, the development of sunlight-based methods for organic synthesis has become imperative. We present a masking enone strategy that effectively suppresses side reactions associated with enone products, enabling the β-selective acylation of alkenes catalyzed by excited-state copper under sunlight or visible light. This reaction yields highly valuable α,β-unsaturated ketones, which can be readily transformed into important building blocks through various conversions. Notably, this method is characterized by its sustainable and eco-friendly energy source, mild reaction conditions, high compatibility with functional groups, and suitability for gram-scale synthesis, making it promising for late-stage modifications of complex molecules. Mechanistic studies indicate that the reaction proceeds via a free radical pathway.</div></div>\",\"PeriodicalId\":94379,\"journal\":{\"name\":\"Organic chemistry frontiers : an international journal of organic chemistry\",\"volume\":\"12 5\",\"pages\":\"Pages 1543-1549\"},\"PeriodicalIF\":0.0000,\"publicationDate\":\"2025-01-08\",\"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/S2052412925000075\",\"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/S2052412925000075","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"","JCRName":"","Score":null,"Total":0}
Visible-light or sunlight photoredox-catalyzed β-selective acylation of alkenes to access α,β-unsaturated ketones†
With increasing concerns regarding the energy crisis and environmental changes, the development of sunlight-based methods for organic synthesis has become imperative. We present a masking enone strategy that effectively suppresses side reactions associated with enone products, enabling the β-selective acylation of alkenes catalyzed by excited-state copper under sunlight or visible light. This reaction yields highly valuable α,β-unsaturated ketones, which can be readily transformed into important building blocks through various conversions. Notably, this method is characterized by its sustainable and eco-friendly energy source, mild reaction conditions, high compatibility with functional groups, and suitability for gram-scale synthesis, making it promising for late-stage modifications of complex molecules. Mechanistic studies indicate that the reaction proceeds via a free radical pathway.