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通过钯催化的环化/偶联串联反应，随后用2,3-二氯-5,6-二氰基-1,4-苯醌进行氧化芳构化反应来合成2-烯基呋喃。

Access to 2-Alkenyl-furans via a Cascade of Pd-Catalyzed Cyclization/Coupling Followed by Oxidative Aromatization with DDQ.

作者信息

Bisek Bartosz, Chaładaj Wojciech

机构信息

Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland.

出版信息

J Org Chem. 2024 May 17;89(10):7275-7279. doi: 10.1021/acs.joc.4c00149. Epub 2024 May 3.

DOI:10.1021/acs.joc.4c00149
PMID:38700491
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC11110045/
Abstract

An unprecedented DDQ-mediated oxidative aromatization of 2-bezylidene-dihydrofurans yielding 2-alkenyl-furans is disclosed. Integration of this transformation with a prior Pd-catalyzed reaction of α-propargylic-β-ketoesters and (hetero)aryl halides into a one-pot cascade process opens a direct modular route to highly substituted 2-vinyl-furans. Experimental and computational studies reveal that the crucial step of the oxidative-aromatization involves facile hydride transfer from the dihydrofuran ring to the O-center of DDQ.

摘要

本文公开了一种前所未有的由2-苄叉基二氢呋喃经DDQ介导的氧化芳构化反应生成2-烯基呋喃的方法。将该转化与先前α-炔丙基-β-酮酯与（杂）芳基卤化物的钯催化反应整合为一锅串联反应，为高取代的2-乙烯基呋喃开辟了一条直接的模块化合成路线。实验和计算研究表明，氧化芳构化的关键步骤涉及二氢呋喃环向DDQ的O中心的便捷氢化物转移。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0a82/11110045/bacbab9e9f87/jo4c00149_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0a82/11110045/bd2d6d05225f/jo4c00149_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0a82/11110045/a4bd05475a01/jo4c00149_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0a82/11110045/c5f84f77efa9/jo4c00149_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0a82/11110045/bacbab9e9f87/jo4c00149_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0a82/11110045/bd2d6d05225f/jo4c00149_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0a82/11110045/a4bd05475a01/jo4c00149_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0a82/11110045/c5f84f77efa9/jo4c00149_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0a82/11110045/bacbab9e9f87/jo4c00149_0001.jpg

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