烯丙基三氟硼酸钾通过无过渡金属 C-N 键裂解直接取代 2-氨基托品

IF 2.8 4区化学 Q1 CHEMISTRY, ORGANIC

Asian Journal of Organic Chemistry Pub Date : 2024-11-01 DOI:10.1002/ajoc.202400386

Qian‐Qian Wu , Yan Wang , Muliang Zhang , Shi‐Kai Tian

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引用次数: 0

摘要

由于氨基的亲核性较差，因此芳香族伯胺的 C-N 键官能化极具挑战性。在此，我们报告了在无过渡金属条件下，通过 C-N 键裂解，2-氨基托品与烯丙基三氟硼酸钾的直接取代反应。2-氨基托品具有独特的非苯类七元芳环，存在于一些天然产物和生物活性分子中。在碳酸氢钠存在下，2-氨基托品的氨基直接被烯丙基三氟硼酸钾取代，以中等至良好的产率得到结构多样的 2-烯丙基托品。该反应不含指导基团、活化基团和过渡金属，为获得取代的托品酮提供了一种便捷的方法。

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Direct Substitution of 2‐Aminotropones with Potassium Allyltrifluoroborates through Transition‐Metal‐Free C−N Bond Cleavage

The poor nucleofugality of the amino group renders the C−N bond functionalization of primary aromatic amines highly challenging. Herein, we report a direct substitution reaction of 2‐aminotropones, bearing a unique non‐benzenoid seven‐membered aromatic ring that exists in some natural products and bioactive molecules, with potassium allyltrifluoroborates through C−N bond cleavage under transition‐metal‐free conditions. The amino group of 2‐aminotropones were directly substituted with potassium allyltrifluoroborates in the presence of sodium bicarbonate, delivering structurally diverse 2‐allyltropones in moderate to good yields. The reaction is free of directing groups, activating groups and transition metals, providing a convenient method to access substituted tropones.

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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.