Preparation of Dibenzofurotropones via Pd-Catalyzed Cyclization

Reactions Pub Date : 2024-01-22 DOI:10.3390/reactions5010005
Yu-Wei Lin, Shiuh‐Tzung Liu
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Abstract

A synthetic approach to dibenzofurotropone derivatives 1 has been developed through the palladium-catalyzed cyclization of (2-bromoaryl)(3-arylfuran-2-yl)methanones 2 via the activation of arylic C–H bonds. Compounds 2 were easily prepared from the palladium-promoted acyl migration and cyclization of (Z)-pent-2-en-4-yn-1-yl acetates 3 in the presence of 1,8-diazabicyclo(5.4.0)undec-7-ene (DBU), followed by oxidative decarbonylation and oxidation with O2. Ten new tropone compounds are reported and these compounds show absorption in the UV-vis region and emission in the visible region.
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通过钯催化环化制备二苯并呋喃丙酮
在钯催化下,(2-溴芳基)(3-芳基呋喃-2-基)甲酮 2 通过丙烯酸 C-H 键活化环化,从而开发出了二苯并呋喃托品衍生物 1 的合成方法。化合物 2 是在 1,8-二氮杂双环(5.4.0)十一-7-烯(DBU)存在下,由钯促进酰基迁移和 (Z)-pent-2-en-4-yn-1-yl 乙酸酯 3 的环化,然后进行氧化脱羰基反应和 O2 氧化反应而轻松制备的。报告中介绍了十种新的托品酮化合物,这些化合物在紫外-可见光区有吸收,在可见光区有发射。
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