通过Rh催化级联Wolff重排和脱羰胺化直接获得氨基环戊烯酮

IF 4 2区化学 Q2 CHEMISTRY, APPLIED

Advanced Synthesis & Catalysis Pub Date : 2025-09-27 DOI:10.1002/adsc.70110

Lvlv Gao, Jianwei Wu, Jian Wang, Enshen Zhang, Yongjia Shang, Xinwei He

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引用次数: 0

摘要

环2 -重氮- 1,3 -二酮和二芳胺的级联反应被有效地开发出来，可以直接获得一系列的2 -氨基环戊烯酮，收率很高（71-90%）。该过程经过一系列的Wolff重排，包括初始的烯酮形成，亲核加成/酮烯醇互变异构，以及Rh2(OAc)4催化的脱羰胺化，然后是氧化过程。广泛的底物与这种温和的反应体系兼容，从而为构建氨基环戊酮的重要骨架提供了一种简便实用的方法。

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Direct Access to Aminocyclopentenones through Rh‐Catalyzed Cascade Wolff Rearrangement and Decarbonylative Amination

The cascade reaction of cyclic 2‐diazo‐1,3‐diketones and diarylamines is efficiently developed, enabling straightforward access to a series of 2‐aminocyclopentenones in good to excellent yields (71–90%). The procedure is proposed to go through a sequence of Wolff rearrangement via initial ketene formation, nucleophilic addition/keto‐enol tautomerization, and Rh2(OAc)4‐catalyzed decarbonylative amination followed by an oxidation process. A broad range of substrates are compatible with this mild reaction system, thereby providing a facile and practical approach for constructing important skeleton of aminocyclopentenone.

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来源期刊

Advanced Synthesis & Catalysis 化学-应用化学

CiteScore

9.40

自引率

7.40%

发文量

447

审稿时长

1.8 months

期刊介绍： Advanced Synthesis & Catalysis (ASC) is the leading primary journal in organic, organometallic, and applied chemistry. The high impact of ASC can be attributed to the unique focus of the journal, which publishes exciting new results from academic and industrial labs on efficient, practical, and environmentally friendly organic synthesis. While homogeneous, heterogeneous, organic, and enzyme catalysis are key technologies to achieve green synthesis, significant contributions to the same goal by synthesis design, reaction techniques, flow chemistry, and continuous processing, multiphase catalysis, green solvents, catalyst immobilization, and recycling, separation science, and process development are also featured in ASC. The Aims and Scope can be found in the Notice to Authors or on the first page of the table of contents in every issue.