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钯催化苯并呋喃与芳基碘化物通过Heck型途径一步实现杂环闭环反应。

One-Step Palladium-Catalyzed Heterocyclic Ring Closure of Benzofurans with Aryl Iodides through a Heck-Type Pathway.

作者信息

Hassan Fathy, Velmurugan Nivedha, Yamane Yusuke, Nic Chormaic Síle, Luscombe Christine K

机构信息

pi-Conjugated Polymers Unit, Okinawa Institute of Science and Technology Graduate University, Onna-son, Okinawa 904-0495, Japan.

Light-Matter Interactions for Quantum Technologies Unit, Okinawa Institute of Science and Technology Graduate University, Onna-son, Okinawa 904-0495, Japan.

出版信息

Org Lett. 2024 Nov 15;26(45):9741-9745. doi: 10.1021/acs.orglett.4c03602. Epub 2024 Nov 6.

DOI:10.1021/acs.orglett.4c03602
PMID:39505830
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC11574844/
Abstract

An operationally simple and robust method for the direct arylation and ring closure of benzofurans is reported. Besides the mild conditions and good reaction yields, the methodology is applicable for a wide range of derivatives using commercially available aryl iodides with complete C regioselectivity. The reaction is proposed to follow a Heck-type oxyarylation mechanism. The facile synthesis method will enable the development of new materials for diverse applications in biology and catalysis and as precursors for organic semiconductors.

摘要

报道了一种用于苯并呋喃直接芳基化和闭环的操作简单且稳健的方法。除了温和的条件和良好的反应产率外,该方法适用于使用市售芳基碘化物的多种衍生物,具有完全的C区域选择性。该反应被认为遵循Heck型氧芳基化机理。这种简便的合成方法将有助于开发用于生物学和催化领域各种应用的新材料,以及作为有机半导体的前体。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b9e7/11574844/2dd9c7886b1a/ol4c03602_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b9e7/11574844/0624e008a44e/ol4c03602_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b9e7/11574844/f20a1a3bd4bd/ol4c03602_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b9e7/11574844/0182ca623af6/ol4c03602_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b9e7/11574844/2dd9c7886b1a/ol4c03602_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b9e7/11574844/0624e008a44e/ol4c03602_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b9e7/11574844/f20a1a3bd4bd/ol4c03602_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b9e7/11574844/0182ca623af6/ol4c03602_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b9e7/11574844/2dd9c7886b1a/ol4c03602_0004.jpg

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本文引用的文献

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Palladium-Catalyzed Regioselective B(9)-Amination of -Carboranes and -Carboranes in HFIP with Broad Nitrogen Sources.钯催化的 HFIP 中 -Carboranes 和 -Carboranes 的 B(9)- 区域选择性胺化反应与广泛的氮源。
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3
Room Temperature C-H Arylation of Benzofurans by Aryl Iodides.
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Org Lett. 2021 Sep 17;23(18):7079-7082. doi: 10.1021/acs.orglett.1c02397. Epub 2021 Sep 2.
4
Hexafluoroisopropanol: the magical solvent for Pd-catalyzed C-H activation.六氟异丙醇:钯催化C-H活化的神奇溶剂。
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