Mingyu Jiang, Yan-En Wang, Yuanyun Gu, Ruyuan Ma, Dan Xiong, Patrick J. Walsh, Jianyou Mao
{"title":"以 LiN(SiMe3)2/KN(SiMe3)2 为介导,基于 Smiles-Rearrangement 方法,从苄基砜和苯甲酸甲酯一步合成二芳基乙炔","authors":"Mingyu Jiang, Yan-En Wang, Yuanyun Gu, Ruyuan Ma, Dan Xiong, Patrick J. Walsh, Jianyou Mao","doi":"10.1021/acs.orglett.4c03492","DOIUrl":null,"url":null,"abstract":"The one-pot synthesis of diphenylacetylene by the reaction of methyl benzoate with 1-(benzylsulfonyl)-3,5-di(trifluoromethyl)benzene was developed. The combination of LiN(SiMe<sub>3</sub>)<sub>2</sub> and KN(SiMe<sub>3</sub>)<sub>2</sub> is key to promoting the reaction. Simply combining methyl benzoate, 1-(benzylsulfonyl)-3,5-di(trifluoromethyl)benzene, LiN(SiMe<sub>3</sub>)<sub>2</sub>, and KN(SiMe<sub>3</sub>)<sub>2</sub> can produce a variety of diaryl acetylenes (28 examples, 18–70% yields).","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"140 1","pages":""},"PeriodicalIF":5.0000,"publicationDate":"2024-11-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Smiles-Rearrangement-Based One-Pot Synthesis of Diarylacetylenes from Benzylic Sulfones and Methyl Benzoates Mediated by LiN(SiMe3)2/KN(SiMe3)2\",\"authors\":\"Mingyu Jiang, Yan-En Wang, Yuanyun Gu, Ruyuan Ma, Dan Xiong, Patrick J. Walsh, Jianyou Mao\",\"doi\":\"10.1021/acs.orglett.4c03492\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"The one-pot synthesis of diphenylacetylene by the reaction of methyl benzoate with 1-(benzylsulfonyl)-3,5-di(trifluoromethyl)benzene was developed. The combination of LiN(SiMe<sub>3</sub>)<sub>2</sub> and KN(SiMe<sub>3</sub>)<sub>2</sub> is key to promoting the reaction. Simply combining methyl benzoate, 1-(benzylsulfonyl)-3,5-di(trifluoromethyl)benzene, LiN(SiMe<sub>3</sub>)<sub>2</sub>, and KN(SiMe<sub>3</sub>)<sub>2</sub> can produce a variety of diaryl acetylenes (28 examples, 18–70% yields).\",\"PeriodicalId\":54,\"journal\":{\"name\":\"Organic Letters\",\"volume\":\"140 1\",\"pages\":\"\"},\"PeriodicalIF\":5.0000,\"publicationDate\":\"2024-11-05\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Organic Letters\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://doi.org/10.1021/acs.orglett.4c03492\",\"RegionNum\":1,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q1\",\"JCRName\":\"CHEMISTRY, ORGANIC\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic Letters","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1021/acs.orglett.4c03492","RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
Smiles-Rearrangement-Based One-Pot Synthesis of Diarylacetylenes from Benzylic Sulfones and Methyl Benzoates Mediated by LiN(SiMe3)2/KN(SiMe3)2
The one-pot synthesis of diphenylacetylene by the reaction of methyl benzoate with 1-(benzylsulfonyl)-3,5-di(trifluoromethyl)benzene was developed. The combination of LiN(SiMe3)2 and KN(SiMe3)2 is key to promoting the reaction. Simply combining methyl benzoate, 1-(benzylsulfonyl)-3,5-di(trifluoromethyl)benzene, LiN(SiMe3)2, and KN(SiMe3)2 can produce a variety of diaryl acetylenes (28 examples, 18–70% yields).
期刊介绍:
Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.