{"title":"铁催化酮和亚胺的还原氘化反应。","authors":"Di-Di Chen, Yu-Tong Gu, Xu-Ya Ma, Xia Tian, Jian-Rong Han, Ying-Zhuang Xu, Qiushi Cheng, Shouxin Liu, Wei Su","doi":"10.1021/acs.orglett.5c01616","DOIUrl":null,"url":null,"abstract":"<p><p>An iron-catalyzed reductive deuteration has been developed for the efficient synthesis of deuterated alcohols and amines. This method employs cost-effective DMSO-<i>d</i><sub>6</sub> as the deuterium source and (Bpin)<sub>2</sub> as the reductant, achieving high levels of D-incorporation (up to 99%) across various substrates, including aryl alkyl ketones, diaryl ketones, aryl aldimines, and aryl ketimines. Mechanistic studies indicate that the ionic iron-boron intermediate generated under conditions of excess base, high temperature, and polar solvents serves as a crucial intermediate for reducing C═O and C═N bonds to form radical anions through single electron transfer (SET), which then undergo deuterium atom transfer (DAT) to afford the reductive deuteration products.</p>","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":" ","pages":"6374-6379"},"PeriodicalIF":5.0000,"publicationDate":"2025-06-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Iron-Catalyzed Reductive Deuteration of Ketones and Imines.\",\"authors\":\"Di-Di Chen, Yu-Tong Gu, Xu-Ya Ma, Xia Tian, Jian-Rong Han, Ying-Zhuang Xu, Qiushi Cheng, Shouxin Liu, Wei Su\",\"doi\":\"10.1021/acs.orglett.5c01616\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<p><p>An iron-catalyzed reductive deuteration has been developed for the efficient synthesis of deuterated alcohols and amines. This method employs cost-effective DMSO-<i>d</i><sub>6</sub> as the deuterium source and (Bpin)<sub>2</sub> as the reductant, achieving high levels of D-incorporation (up to 99%) across various substrates, including aryl alkyl ketones, diaryl ketones, aryl aldimines, and aryl ketimines. Mechanistic studies indicate that the ionic iron-boron intermediate generated under conditions of excess base, high temperature, and polar solvents serves as a crucial intermediate for reducing C═O and C═N bonds to form radical anions through single electron transfer (SET), which then undergo deuterium atom transfer (DAT) to afford the reductive deuteration products.</p>\",\"PeriodicalId\":54,\"journal\":{\"name\":\"Organic Letters\",\"volume\":\" \",\"pages\":\"6374-6379\"},\"PeriodicalIF\":5.0000,\"publicationDate\":\"2025-06-20\",\"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.5c01616\",\"RegionNum\":1,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"2025/6/6 0:00:00\",\"PubModel\":\"Epub\",\"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.5c01616","RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"2025/6/6 0:00:00","PubModel":"Epub","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
Iron-Catalyzed Reductive Deuteration of Ketones and Imines.
An iron-catalyzed reductive deuteration has been developed for the efficient synthesis of deuterated alcohols and amines. This method employs cost-effective DMSO-d6 as the deuterium source and (Bpin)2 as the reductant, achieving high levels of D-incorporation (up to 99%) across various substrates, including aryl alkyl ketones, diaryl ketones, aryl aldimines, and aryl ketimines. Mechanistic studies indicate that the ionic iron-boron intermediate generated under conditions of excess base, high temperature, and polar solvents serves as a crucial intermediate for reducing C═O and C═N bonds to form radical anions through single electron transfer (SET), which then undergo deuterium atom transfer (DAT) to afford the reductive deuteration products.
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.
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