{"title":"Copper-catalyzed nucleophilic methoxylation of DMAN bromides as a route to highly basic naphthalene proton sponges","authors":"Andrey V. Marchenko, Valery A. Ozeryanskii","doi":"10.1016/j.tetlet.2024.155394","DOIUrl":null,"url":null,"abstract":"<div><div>The possibility of direct copper-catalyzed bromine-to-methoxy exchange to afford highly basic (poly)methoxy substituted 1,8-bis(dimethylamino)naphthalenes (DMANs or “proton sponges”) has been studied for the first time. The thus synthesized known or newly designed compounds are superbases with the basicities ranging within 19–23 p<em>K</em><sub>a</sub> units in MeCN. Selected chemical behavior of mono-methoxylated DMANs as to methoxy group cleavage or regioselective lithiation is also reported.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"154 ","pages":"Article 155394"},"PeriodicalIF":1.5000,"publicationDate":"2025-01-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Tetrahedron Letters","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S0040403924004891","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"2024/11/27 0:00:00","PubModel":"Epub","JCR":"Q3","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0
Abstract
The possibility of direct copper-catalyzed bromine-to-methoxy exchange to afford highly basic (poly)methoxy substituted 1,8-bis(dimethylamino)naphthalenes (DMANs or “proton sponges”) has been studied for the first time. The thus synthesized known or newly designed compounds are superbases with the basicities ranging within 19–23 pKa units in MeCN. Selected chemical behavior of mono-methoxylated DMANs as to methoxy group cleavage or regioselective lithiation is also reported.
期刊介绍：
Tetrahedron Letters provides maximum dissemination of outstanding developments in organic chemistry. The journal is published weekly and covers developments in techniques, structures, methods and conclusions in experimental and theoretical organic chemistry. Rapid publication of timely and significant research results enables researchers from all over the world to transmit quickly their new contributions to large, international audiences.
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