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钯催化脂肪族炔烃与芳基噻蒽盐的羰基化Sonogashira偶联反应合成炔酮和呋喃酮

Palladium-Catalyzed Carbonylative Sonogashira Coupling of Aliphatic Alkynes and Aryl Thianthrenium Salts to Alkynones and Furanones.

作者信息

Zhao Yan-Hua, Gu Xing-Wei, Wu Xiao-Feng

机构信息

Leibniz-Institut für Katalyse e.V., Albert-Einstein-Straße 29a, 18059 Rostock, Germany.

Dalian National Laboratory for Clean Energy, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023, Liaoning, China.

出版信息

Org Lett. 2024 Dec 20;26(50):10702-10707. doi: 10.1021/acs.orglett.4c03519. Epub 2024 Dec 9.

DOI:10.1021/acs.orglett.4c03519
PMID:39651552
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC11667721/
Abstract

Herein, we developed a mild and efficient palladium-catalyzed carbonylative Sonogashira coupling of aryl thianthrenium salts with aliphatic alkynes and benzyl acetylene toward alkynones and furanones. Various desired products were prepared in good yields with broad functional group tolerance including the bromide group. In the case of using benzyl acetylene, the corresponding furanones can be obtained in good yields under the same conditions with two molecules of CO inserted.

摘要

在此,我们开发了一种温和且高效的钯催化芳基噻蒽盐与脂肪族炔烃和苄基乙炔的羰基化Sonogashira偶联反应,用于制备炔酮和呋喃酮。各种所需产物均以良好的产率制备得到,具有广泛的官能团耐受性,包括溴基团。在使用苄基乙炔的情况下,在相同条件下插入两分子CO时,可以以良好的产率获得相应的呋喃酮。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6916/11667721/c435081ebb96/ol4c03519_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6916/11667721/c435081ebb96/ol4c03519_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6916/11667721/c435081ebb96/ol4c03519_0001.jpg

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本文引用的文献

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Palladium-Catalyzed Carbonylative Sonogashira Coupling of Aryl Thianthrenium Salts with Arylalkynes.钯催化芳基噻蒽鎓盐与芳基炔烃的羰基化Sonogashira偶联反应
Org Lett. 2024 Aug 2;26(30):6507-6511. doi: 10.1021/acs.orglett.4c02440. Epub 2024 Jul 18.
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Nucleophilic functionalization of thianthrenium salts under basic conditions.噻蒽鎓盐在碱性条件下的亲核官能团化反应。
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Transition-metal-free C-S bond cleavage and transformation of organosulfur compounds.
无过渡金属参与的 C-S 键断裂及有机硫化合物的转化。
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Palladium-Catalyzed Carbonylative Synthesis of Diaryl Ketones from Arenes and Arylboronic Acids through C(sp)-H Thianthrenation.钯催化芳烃和芳基硼酸通过 C(sp)-H 噻吩并化反应合成二芳基酮
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Organothianthrenium salts: synthesis and utilization.有机噻蒽鎓盐:合成与应用
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Metal- and Strain-Free Bioorthogonal Cycloaddition of o-Diones with Furan-2(3H)-one as Anionic Cycloaddend.无金属和应变的 o-二酮与呋喃-2(3H)-酮的生物正交环加成反应作为阴离子环加成物。
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Sustainable Thioetherification via Electron Donor-Acceptor Photoactivation Using Thianthrenium Salts.通过使用噻蒽鎓盐的电子给体-受体光活化实现可持续的硫醚化反应。
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