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锂促进钯催化的α-高炔丙基-β-酮酯与芳基溴化物和三氟甲磺酸酯的5-环化/偶联反应。

Lithium Enables Pd-Catalyzed 5 Cyclization/Coupling of α-Homopropargyl-β-ketoesters with Aryl Bromides and Triflates.

作者信息

Bisek Bartosz, Kochaniak Katarzyna, 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

Org Lett. 2024 Oct 4;26(39):8254-8259. doi: 10.1021/acs.orglett.4c02846. Epub 2024 Sep 19.

DOI:10.1021/acs.orglett.4c02846
PMID:39298715
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC11459523/
Abstract

Tight chelation of enolate by lithium alters the selectivity of tandem palladium-catalyzed cyclization/coupling of terminal α-homopropargyl-β-ketoesters with aryl halides. In the presence of LiOH, substituted cyclopentenes are preferentially formed via 5- carbocyclization, in contrast to the 6 oxocyclization exclusively observed in the absence of a hard, chelating metal center. The disclosed transformation, featuring mild conditions and broad functional group tolerance, can be applied for a variety of (hetero)aryl bromides as well as aryl and vinyl triflates.

摘要

烯醇化物与锂的紧密螯合改变了钯催化的末端α-高炔丙基-β-酮酯与芳基卤化物的串联环化/偶联反应的选择性。在LiOH存在下，通过5-碳环化优先形成取代的环戊烯，这与在没有硬螯合金属中心时仅观察到的6-氧环化形成对比。所公开的转化反应条件温和，对官能团的耐受性广，可应用于多种（杂）芳基溴化物以及芳基和乙烯基三氟甲磺酸酯。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ed76/11459523/ea560fba4fb8/ol4c02846_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ed76/11459523/9e6bf5230ca8/ol4c02846_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ed76/11459523/b33371facb00/ol4c02846_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ed76/11459523/ea560fba4fb8/ol4c02846_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ed76/11459523/9e6bf5230ca8/ol4c02846_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ed76/11459523/b33371facb00/ol4c02846_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ed76/11459523/ea560fba4fb8/ol4c02846_0003.jpg

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