钯催化的 1-炔基-2-碘-d-葡萄糖醛的羰基环化反应。

IF 4.9 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2024-10-11 Epub Date: 2024-09-30 DOI:10.1021/acs.orglett.4c03337

Milene M Hornink, Giuseppe E Figlino, Mônica F Z J Toledo, Daniel C Pimenta, Hélio A Stefani

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引用次数: 0

摘要

级联反应是合成杂环分子的重要合成工具，尤其是钯催化的级联反应。在此，我们报告了钯催化的新型 1-炔基-2-碘-d-葡萄糖的氨基羰基环化反应，该反应在各种胺类亲核物存在下发生串联羰基环化。我们使用了多种芳香族和脂肪族胺作为偶联剂，从而选择性地高产合成了与吡啶酮融合的苷类化合物。提出了一个合理的机理，即通过串联钯氨基羰基化反应，然后在钯催化下进行内二元环化反应。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

Palladium-Catalyzed Carbonylative Cyclization of 1-Alkynyl-2-iodo-d-glucal.

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Palladium-Catalyzed Carbonylative Cyclization of 1-Alkynyl-2-iodo-d-glucal.

Cascade reactions are important synthetic tools for the synthesis of heterocyclic molecules, particularly those catalyzed by palladium. Herein, we report a palladium-catalyzed aminocarbonylative cyclization of new 1-alkynyl-2-iodo-d-glucals, which undergo a tandem carbonylative cyclization in the presence of various amine nucleophiles. A broad range of aromatic and aliphatic amines were applied as coupling partners, resulting in the selective and high-yield synthesis of glycosides fused to pyridinones. A plausible mechanism is proposed, proceeding via a tandem palladium aminocarbonylation followed by a palladium-catalyzed endo-dig cyclization.

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来源期刊

Organic Letters 化学-有机化学

CiteScore

9.30

自引率

11.50%

发文量

1607

审稿时长

1.5 months

期刊介绍： Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.