Transition-Metal-Free Direct α-Arylation of Weinreb-type Amides with Arylboronic Acids through Aza-oxyallyl Cation Intermediates.

IF 3.3 2区 化学 Q1 CHEMISTRY, ORGANIC The Journal of Organic Chemistry Pub Date : 2024-09-20 Epub Date: 2024-08-28 DOI:10.1021/acs.joc.4c01391
Jiali Gao, Minmin Hu, Yuzhi Wang, Sanzhong Luo, Xueling Mi
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Abstract

Here, we report an efficient transition-metal-free C(sp2)-C(sp3) Suzuki-Miyaura-type cross-coupling between α-halo Weinreb-type amides and arylboronic acids. The reaction is carried out by capturing active aza-oxyallyl cation (AOAC) with arylboronic acid to form a boron "ate" complex, followed by 1,4-migration to give α-aryl amides with good yields.

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通过氮氧烯丙基阳离子中间体,用芳基硼酸对 Weinreb 型酰胺进行无过渡金属直接 α-芳基化。
在此,我们报告了一种 α-halo Weinreb 型酰胺与芳基硼酸之间的高效无过渡金属 C(sp2)-C(sp3) Suzuki-Miyaura 型交叉偶联反应。该反应是通过捕获芳基硼酸中的活性偶氮氧烯丙基阳离子(AOAC)来形成硼 "阿特 "络合物,然后进行 1,4 迁移,最终得到α-芳基酰胺,收率很高。
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来源期刊
The Journal of Organic Chemistry
The Journal of Organic Chemistry 化学-有机化学
CiteScore
6.20
自引率
11.10%
发文量
1467
审稿时长
2 months
期刊介绍: The Journal of Organic Chemistry welcomes original contributions of fundamental research in all branches of the theory and practice of organic chemistry. In selecting manuscripts for publication, the editors place emphasis on the quality and novelty of the work, as well as the breadth of interest to the organic chemistry community.
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