{"title":"N-Protonated Acridinium Catalyst Enables Anti-Markovnikov Hydration of Unconjugated Tri- and Disubstituted Olefins.","authors":"Boris Alexander van der Worp, Tobias Ritter","doi":"10.1021/jacs.4c18185","DOIUrl":null,"url":null,"abstract":"<p><p>The preparation of alcohols with anti-Markovnikov selectivity directly from olefins and water is a sought-after reaction due to its atom-economy and potential cost-effectiveness. Herein, we present the first general method for direct, catalytic anti-Markovnikov hydration of unconjugated tri- and disubstituted olefins. The key advancement is made possible by an oxidative (<i>E</i>*<sub>red</sub> = 2.15 V) <i>N</i>-H acridinium catalyst, which allowed for the functionalization of alkenes that were previously unreactive in such transformations due to their high oxidation potential. The developed protocol is not limited to hydration but also enables other hydrofunctionalizations, such as hydroetherifications, following the same mechanistic pathway.</p>","PeriodicalId":49,"journal":{"name":"Journal of the American Chemical Society","volume":" ","pages":"4736-4742"},"PeriodicalIF":14.4000,"publicationDate":"2025-02-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11826999/pdf/","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Journal of the American Chemical Society","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1021/jacs.4c18185","RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"2025/1/31 0:00:00","PubModel":"Epub","JCR":"Q1","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
引用次数: 0
Abstract
The preparation of alcohols with anti-Markovnikov selectivity directly from olefins and water is a sought-after reaction due to its atom-economy and potential cost-effectiveness. Herein, we present the first general method for direct, catalytic anti-Markovnikov hydration of unconjugated tri- and disubstituted olefins. The key advancement is made possible by an oxidative (E*red = 2.15 V) N-H acridinium catalyst, which allowed for the functionalization of alkenes that were previously unreactive in such transformations due to their high oxidation potential. The developed protocol is not limited to hydration but also enables other hydrofunctionalizations, such as hydroetherifications, following the same mechanistic pathway.
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The flagship journal of the American Chemical Society, known as the Journal of the American Chemical Society (JACS), has been a prestigious publication since its establishment in 1879. It holds a preeminent position in the field of chemistry and related interdisciplinary sciences. JACS is committed to disseminating cutting-edge research papers, covering a wide range of topics, and encompasses approximately 19,000 pages of Articles, Communications, and Perspectives annually. With a weekly publication frequency, JACS plays a vital role in advancing the field of chemistry by providing essential research.
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