{"title":"Deaminative Functionalization of Olefins and Dienes with Katritzky Salts: A Highly Selective Route to Diverse Deuterium-Labeled Molecules","authors":"Farrukh Sajjad, , , Guanfeng Zhou, , , Congyin Yan, , , Bingjie Shen, , , Hanfu Liu, , , Wen Xu, , , Xinni Zheng, , , Cheng Lu*, , and , Tie-Gen Chen*, ","doi":"10.1021/acs.orglett.5c03565","DOIUrl":null,"url":null,"abstract":"<p >Herein, we report a deaminative alkylation of olefins, followed by deuteration that allows the formation of sp<sup>3</sup>–sp<sup>3</sup> architectures. This protocol enables the previously unexploited functionalization of dienes with pyridinium salts, providing rapid access to complex molecules from bulk chemicals in a highly selective manner. Notably, the diversification of commercially available drug molecules particularly through deuteration is widely recognized as an effective strategy for drug discovery. Gratifyingly, this reaction facilitated the alkylation of drug- and amino acid-derived pyridinium salts, demonstrating both its synthetic versatility and potential utility in drug development.</p>","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"27 41","pages":"11543–11548"},"PeriodicalIF":5.0000,"publicationDate":"2025-10-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic Letters","FirstCategoryId":"92","ListUrlMain":"https://pubs.acs.org/doi/10.1021/acs.orglett.5c03565","RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0
Abstract
Herein, we report a deaminative alkylation of olefins, followed by deuteration that allows the formation of sp3–sp3 architectures. This protocol enables the previously unexploited functionalization of dienes with pyridinium salts, providing rapid access to complex molecules from bulk chemicals in a highly selective manner. Notably, the diversification of commercially available drug molecules particularly through deuteration is widely recognized as an effective strategy for drug discovery. Gratifyingly, this reaction facilitated the alkylation of drug- and amino acid-derived pyridinium salts, demonstrating both its synthetic versatility and potential utility in drug development.
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.