锌催化乙烯基叠氮化物的环异构化/甲基化：末端和氘化烯基呋喃框架的组装

IF 4 2区化学 Q2 CHEMISTRY, APPLIED

Advanced Synthesis & Catalysis Pub Date : 2025-09-26 DOI:10.1002/adsc.70112

Shaotong Qiu , Jiangan Liu , Dan Tang , Yangxin Mao , Zhicheng Yang , Changyuan Zhang , Hu Zhou

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引用次数: 0

摘要

研究了一种前所未有的锌催化的乙烯基叠氮化物与酶的环异构化/甲基化反应。该方案具有价格低廉，催化剂毒性小，效率高，反应条件温和的特点，为获得各种生物活性相关的终端和氘化烯基呋喃提供了一种实用的合成方法，收率高达99%，氘掺入率高达94%。该反应可通过环异构化、环丙烷化和环断裂等过程进行。通过将所得分子转化为选择性半氘化和非氘化呋喃骨架，进一步证明了该反应的实用性。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

Zn‐Catalyzed Cycloisomerization/Methylenation of Enyone with Vinyl Azide: Assembly of Terminal and Deuterated Alkenyl Furan Framework

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Zn‐Catalyzed Cycloisomerization/Methylenation of Enyone with Vinyl Azide: Assembly of Terminal and Deuterated Alkenyl Furan Framework

An unprecedented zinc‐catalyzed cycloisomerization/methylenation reaction of enynone with vinyl azide is developed. Featuring inexpensive, less‐toxic catalyst, high efficiency, and mild reaction conditions, this protocol provides a practical synthetic method to access various bioactivity‐related terminal and deuterated alkenyl furans in up to 99% yield and 94% level of deuterium incorporation. The reaction is proposed to proceed through cycloisomerization, cyclopropanation, and ring fragmentation processes. Utility of this reaction is further demonstrated by transformation of the obtained molecules into selectively semi‐deuterated and non‐deuterated furan skeletons.

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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.