Chun-Yan Wu , Xiang-Long Chen , Huai-Yu Wang , Dong-Sheng Yang , Shi-Yi Zhuang , You Zhou , Zhi-Cheng Yu , Yan-Dong Wu , Xiao Geng , An-Xin Wu
{"title":"BrCF2CO2Et的双重作用：二氟卡宾能够从亚磺酰亚砜中获得α-三氟甲基酮†","authors":"Chun-Yan Wu , Xiang-Long Chen , Huai-Yu Wang , Dong-Sheng Yang , Shi-Yi Zhuang , You Zhou , Zhi-Cheng Yu , Yan-Dong Wu , Xiao Geng , An-Xin Wu","doi":"10.1039/d3qo00609c","DOIUrl":null,"url":null,"abstract":"<div><p>A transition metal and external fluorine anion-free method has been developed for the efficient trifluoromethylation of sulfoxonium ylides with BrCF<sub>2</sub>CO<sub>2</sub>Et to afford α-trifluoromethyl ketones. Mechanistic investigation revealed that taking advantage of the dual role of BrCF<sub>2</sub>CO<sub>2</sub>Et, which concurrently acts as a CF<sub>2</sub> and F source, is key to realizing this reaction. This method is applicable to the late-stage modification of biologically active compounds and can be readily scaled up.</p></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"10 15","pages":"Pages 3741-3745"},"PeriodicalIF":0.0000,"publicationDate":"2023-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Dual role of BrCF2CO2Et: difluorocarbene-enabled access to α-trifluoromethyl ketones from sulfoxonium ylides†\",\"authors\":\"Chun-Yan Wu , Xiang-Long Chen , Huai-Yu Wang , Dong-Sheng Yang , Shi-Yi Zhuang , You Zhou , Zhi-Cheng Yu , Yan-Dong Wu , Xiao Geng , An-Xin Wu\",\"doi\":\"10.1039/d3qo00609c\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><p>A transition metal and external fluorine anion-free method has been developed for the efficient trifluoromethylation of sulfoxonium ylides with BrCF<sub>2</sub>CO<sub>2</sub>Et to afford α-trifluoromethyl ketones. Mechanistic investigation revealed that taking advantage of the dual role of BrCF<sub>2</sub>CO<sub>2</sub>Et, which concurrently acts as a CF<sub>2</sub> and F source, is key to realizing this reaction. This method is applicable to the late-stage modification of biologically active compounds and can be readily scaled up.</p></div>\",\"PeriodicalId\":94379,\"journal\":{\"name\":\"Organic chemistry frontiers : an international journal of organic chemistry\",\"volume\":\"10 15\",\"pages\":\"Pages 3741-3745\"},\"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/S2052411023009197\",\"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/S2052411023009197","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"","JCRName":"","Score":null,"Total":0}
Dual role of BrCF2CO2Et: difluorocarbene-enabled access to α-trifluoromethyl ketones from sulfoxonium ylides†
A transition metal and external fluorine anion-free method has been developed for the efficient trifluoromethylation of sulfoxonium ylides with BrCF2CO2Et to afford α-trifluoromethyl ketones. Mechanistic investigation revealed that taking advantage of the dual role of BrCF2CO2Et, which concurrently acts as a CF2 and F source, is key to realizing this reaction. This method is applicable to the late-stage modification of biologically active compounds and can be readily scaled up.
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