铜催化DMAN溴化物的亲核甲氧基化制备高碱性萘质子海绵的途径

IF 1.4 4区化学 Q3 CHEMISTRY, ORGANIC Tetrahedron Letters Pub Date : 2025-01-15 Epub Date: 2024-11-27 DOI:10.1016/j.tetlet.2024.155394

Andrey V. Marchenko, Valery A. Ozeryanskii

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引用次数: 0

摘要

首次研究了直接铜催化溴-甲氧基交换制备高碱性（聚）甲氧基取代的1,8-二（二甲氨基）萘（DMANs或“质子海绵”）的可能性。由此合成的已知或新设计的化合物是在MeCN中碱度在19-23 pKa单位之间的超碱。还报道了单甲氧基化DMANs在甲氧基裂解或区域选择性锂化方面的选择性化学行为。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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Copper-catalyzed nucleophilic methoxylation of DMAN bromides as a route to highly basic naphthalene proton sponges

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 pK_a units in MeCN. Selected chemical behavior of mono-methoxylated DMANs as to methoxy group cleavage or regioselective lithiation is also reported.

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来源期刊

Tetrahedron Letters 化学-有机化学

CiteScore

3.50

自引率

5.60%

发文量

521

审稿时长

28 days

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.