吡啶-硼基自由基催化的炔拴环丙基酮 [3 + 2] 环加成反应

IF 4.4 2区化学 Q2 CHEMISTRY, APPLIED Advanced Synthesis & Catalysis Pub Date : 2024-10-04 DOI:10.1002/adsc.202401015

Hua Huang, Xiao-Die An, Yi-Fan Wang, Yun-Xuan Tan, Ping Tian

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引用次数: 0

摘要

双环[3.3.0]辛烷是各种具有生物活性的天然化合物中的重要结构基团。在本研究中，我们首次通过吡啶-硼烷自由基催化，以无金属形式实现了炔拴环丙基酮的[3 + 2]环加成反应，从而高效、广泛地获得了双环[3.3.0]辛烷。该反应的特点是通过吡啶-硼烷自由基生成酮基，以及连续的 5-exo-dig 和 5-exo-trig 自由基级联过程。

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Pyridine‐Boryl Radical‐Catalyzed [3 + 2] Cycloadditions of Alkyne‐Tethered Cyclopropyl Ketones

Bicyclo[3.3.0]octanes represent crucial structural motifs found in various bioactive natural compounds. In this study, we present the first metal‐free formal [3 + 2] cycloadditions of alkyne‐tethered cyclopropyl ketones via pyridine‐boryl radical catalysis, affording bicyclo[3.3.0]octanes with high efficiency and broad substrate scope. This reaction features the generation of ketyl radical by pyridine‐boryl radical and a consecutive 5‐exo‐dig and 5‐exo‐trig radical cascade process.

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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.