铁氰化钾介导的儿茶酚与2-吲哚和苯并呋喃酮的区域选择性交叉脱氢偶联

IF 2.2 3区化学 Q2 CHEMISTRY, ORGANIC

Tetrahedron Pub Date : 2025-07-17 DOI:10.1016/j.tet.2025.134831

Tomoyuki Iwakiri , Mai Akakabe , Akifumi Inoue , Yoshihiro Sohtome , Mikiko Sodeoka

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引用次数: 0

摘要

儿茶酚的交叉脱氢偶联反应为合成多取代儿茶酚提供了一条直接途径。虽然原位氧化邻醌已经发展了儿茶酚的CDC反应，但控制区域选择性仍然具有挑战性。在此，我们详细介绍了我们对4-取代儿茶酚与持久性自由基前体，2-吲哚和苯并呋喃酮的C(6)选择性CDC反应的研究。我们的优化研究基于机理控制实验，开发了一种使用溶解O2和亚化学计量量的K3[Fe(CN)6]的协同氧化体系，这扩大了4-取代儿茶酚C(6)选择性CDC反应的底物范围。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

Potassium ferricyanide-mediated regioselective cross-dehydrogenative coupling of catechols with 2-oxindoles and benzofuranones

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Potassium ferricyanide-mediated regioselective cross-dehydrogenative coupling of catechols with 2-oxindoles and benzofuranones

Cross dehydrogenative coupling (CDC) reactions of catechols offer a direct route to multi-substituted catechols. While in situ oxidation to ortho-quinones has advanced CDC reactions of catechols, controlling regioselectivity remains challenging. Herein, we present details of our investigations into the C(6)-selective CDC reaction of 4-substituted catechols with the persistent radical precursors, 2-oxindoles and benzofuranones. Our optimization studies, based on mechanistic control experiments, led to the development of a cooperative oxidation system using dissolved O₂ and a sub-stoichiometric amount of K₃[Fe(CN)₆], which expands the substrate scope of the C(6)-selective CDC reaction of 4-substituted catechols.

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来源期刊

Tetrahedron 化学-有机化学

CiteScore

3.90

自引率

4.80%

发文量

439

审稿时长

34 days

期刊介绍： Tetrahedron publishes full accounts of research having outstanding significance in the broad field of organic chemistry and its related disciplines, such as organic materials and bio-organic chemistry. Regular papers in Tetrahedron are expected to represent detailed accounts of an original study having substantially greater scope and details than that found in a communication, as published in Tetrahedron Letters. Tetrahedron also publishes thematic collections of papers as special issues and ''Reports'', commissioned in-depth reviews providing a comprehensive overview of a research area.