通过区域选择性直接芳基化合成 3-芳基取代的三咪唑三嗪

IF 2.8 4区化学 Q1 CHEMISTRY, ORGANIC Asian Journal of Organic Chemistry Pub Date : 2024-07-01 DOI:10.1002/ajoc.202400082

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引用次数: 0

摘要

在以 K2CO3 为碱和由 Pd(OAc)2 和 P(2-呋喃)3 组成的催化剂前体存在下，成功地在 DMA 中用（杂）芳基卤化物对三咪唑并[1,2-a:1',2'-c:1'',2''-e][1,3,5]三嗪（1）的 3 位进行了一般和方便的选择性直接芳基化反应。电子贫乏和富集的（杂）芳基，包括强烈失活和立体包被的 2,4,6-三甲氧基苯基单元，都能很好地容纳在亲电伴侣中。这项合成研究获得的数据支持一种反应机理，即芳基钯（II）卤化物亲电攻击三嗪环。

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Synthesis of 3‐Aryl Substituted Triimidazotriazines via Regioselective Direct Arylation

A general and convenient selective direct arylation of the 3‐position of triimidazo[1,2‐a:1’,2’‐c:1’’,2’’‐e][1,3,5]triazine (1) with (hetero)aryl halides in DMA was successfully achieved in the presence of K₂CO₃ as the base and a catalyst precursor consisting of Pd(OAc)₂ and P(2‐furyl)₃. Electron‐poor and ‐rich (hetero)aryl moieties, including the strongly deactivated and sterically encumbered 2,4,6‐trimethoxyphenyl unit, are well tolerated in the electrophilic partner. The data obtained in this synthetic study support a reaction mechanism involving an electrophilic attack of an arylpalladium‐(II) halide species onto the triazine ring.

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来源期刊

Asian Journal of Organic Chemistry CHEMISTRY, ORGANIC-

CiteScore

4.70

自引率

3.70%

发文量

372

期刊介绍： Organic chemistry is the fundamental science that stands at the heart of chemistry, biology, and materials science. Research in these areas is vigorous and truly international, with three major regions making almost equal contributions: America, Europe and Asia. Asia now has its own top international organic chemistry journal—the Asian Journal of Organic Chemistry (AsianJOC) The AsianJOC is designed to be a top-ranked international research journal and publishes primary research as well as critical secondary information from authors across the world. The journal covers organic chemistry in its entirety. Authors and readers come from academia, the chemical industry, and government laboratories.