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由芳香醛和末端炔烃光催化合成茚酮

Photo-Catalyzed Synthesis of Indanones from Aromatic Aldehydes and Terminal Alkynes.

作者信息

Babawale Florence, Ghosh Indrajit, König Burkhard

机构信息

Fakultät für Chemie und Pharmazie, Universität Regensburg, Regensburg 93040, Germany.

出版信息

J Org Chem. 2025 Oct 3;90(39):13885-13890. doi: 10.1021/acs.joc.5c01749. Epub 2025 Sep 22.

DOI:10.1021/acs.joc.5c01749
PMID:40980870
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC12501931/
Abstract

Indanones are key structural motifs in pharmaceuticals and bioactive natural products, making their efficient synthesis a subject of continued interest. Conventional methods typically rely on transition-metal catalysis, prefunctionalized substrates, and multiple redox steps. Herein, we report a photochemical C-H annulation strategy for the direct synthesis of indanones from simple, unmodified aromatic aldehydes and terminal alkynes. The reaction proceeds under 365 nm light using tetrabutylphosphonium decatungstate ([BuP]WO, TBPDT) as a hydrogen atom transfer (HAT) photocatalyst. This prefunctionalization-free protocol tolerates a broad range of substrates, eliminates the need for additional redox steps, and expands the toolbox for sustainable indanone synthesis.

摘要

茚满酮是药物和生物活性天然产物中的关键结构基序,因此其高效合成一直是人们持续关注的课题。传统方法通常依赖于过渡金属催化、预官能化底物和多个氧化还原步骤。在此,我们报道了一种光化学C-H环化策略,用于从简单的、未修饰的芳香醛和末端炔烃直接合成茚满酮。该反应在365 nm光下进行,使用四丁基鏻十钨酸盐([BuP]WO,TBPDT)作为氢原子转移(HAT)光催化剂。这种无需预官能化的方法能耐受多种底物,无需额外的氧化还原步骤,并扩展了可持续合成茚满酮的方法库。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8ff6/12501931/d796fe4404df/jo5c01749_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8ff6/12501931/714cca43d2bc/jo5c01749_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8ff6/12501931/4ce9e4acbb25/jo5c01749_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8ff6/12501931/d796fe4404df/jo5c01749_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8ff6/12501931/714cca43d2bc/jo5c01749_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8ff6/12501931/4ce9e4acbb25/jo5c01749_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8ff6/12501931/d796fe4404df/jo5c01749_0002.jpg

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本文引用的文献

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Tetrabutylammonium decatungstate (TBADT), a compelling and trailblazing catalyst for visible-light-induced organic photocatalysis.四丁基铵十钨酸盐(TBADT),一种用于可见光诱导有机光催化的引人注目的开创性催化剂。
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