乙烯基-酰基1,5-钯移位使醛的酰胺化和酯化。

IF 3.3 2区化学 Q1 CHEMISTRY, ORGANIC

Journal of Organic Chemistry Pub Date : 2025-07-02 DOI:10.1021/acs.joc.5c01114

Yaru Fang,Qifan Guan,Meiyu Chen,Shan Yuan,Xueliang Huang

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引用次数: 0

摘要

我们报道了一种前所未有的合成途径，通过乙烯基到酰基1,5-钯的迁移来合成二氢苯并呋喃和吲哚酰基化合物。这一转变是由炔插入引发的，触发关键的1,5-钯迁移，生成反应性酰基钯中间体。这些中间体经过胺和醇的有效捕获，产生相应的酰胺和酯类产品。值得注意的是，该产物可以进一步构建具有显著药物潜力的八元内酰胺支架，突出了该策略在复杂分子合成中的广泛实用性。

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Vinyl-to-Acyl 1,5-Palladium Shift Enabled Amidation and Esterification of Aldehydes.

We report an unprecedented synthetic route to dihydrobenzofuran and indoline acyl compounds via vinyl-to-acyl 1,5-palladium migration. This transformation is initiated by alkyne insertion, triggering the key 1,5-palladium migration to generate reactive acyl palladium intermediates. These intermediates undergo efficient trapping by amines and alcohols to afford the corresponding amide and ester-type products. Notably, the product can be further elaborated to construct eight-membered lactam scaffolds with significant pharmaceutical potential, highlighting the broad utility of this strategy in complex molecule synthesis.

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来源期刊

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： 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.