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镍催化2-氟苯并呋喃与芳基硼酸通过芳香碳-氟键活化进行交叉偶联反应。

Nickel-catalyzed cross-coupling of 2-fluorobenzofurans with arylboronic acids via aromatic C-F bond activation.

作者信息

Fujita Takeshi, Yabuki Haruna, Morioka Ryutaro, Fuchibe Kohei, Ichikawa Junji

机构信息

The Institute for Solid State Physics, The University of Tokyo, 5-1-5 Kashiwanoha, Kashiwa, Chiba 277-8581, Japan.

Division of Chemistry, Faculty of Pure and Applied Sciences, University of Tsukuba, 1-1-1 Tennodai, Tsukuba, Ibaraki 305-8571, Japan.

出版信息

Beilstein J Org Chem. 2025 Jan 15;21:146-154. doi: 10.3762/bjoc.21.8. eCollection 2025.

DOI:10.3762/bjoc.21.8
PMID:39834895
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC11744694/
Abstract

2-Fluorobenzofurans underwent efficient nickel-catalyzed coupling with arylboronic acids through the activation of aromatic C-F bonds. This method allowed us to successfully synthesize a range of 2-arylbenzofurans with various substituents. The reaction, which proceeded under mild conditions, involved β-fluorine elimination from nickelacyclopropanes formed by the interaction of 2-fluorobenzofurans with zero-valent nickel species. This protocol facilitates orthogonal coupling reactions of aromatic C-F and C-Br bonds with arylboronic acids.

摘要

2-氟苯并呋喃通过芳族C-F键的活化，在镍催化下与芳基硼酸进行了高效偶联反应。该方法使我们能够成功合成一系列带有各种取代基的2-芳基苯并呋喃。该反应在温和条件下进行，涉及由2-氟苯并呋喃与零价镍物种相互作用形成的镍杂环丙烷的β-氟消除反应。该方案促进了芳族C-F和C-Br键与芳基硼酸的正交偶联反应。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f9b1/11744694/e30d97e83912/Beilstein_J_Org_Chem-21-146-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f9b1/11744694/4465507cff29/Beilstein_J_Org_Chem-21-146-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f9b1/11744694/9aaef22ef9ad/Beilstein_J_Org_Chem-21-146-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f9b1/11744694/382fef7b58ef/Beilstein_J_Org_Chem-21-146-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f9b1/11744694/01bf52fe841a/Beilstein_J_Org_Chem-21-146-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f9b1/11744694/1fbca0e36d56/Beilstein_J_Org_Chem-21-146-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f9b1/11744694/e30d97e83912/Beilstein_J_Org_Chem-21-146-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f9b1/11744694/4465507cff29/Beilstein_J_Org_Chem-21-146-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f9b1/11744694/9aaef22ef9ad/Beilstein_J_Org_Chem-21-146-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f9b1/11744694/382fef7b58ef/Beilstein_J_Org_Chem-21-146-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f9b1/11744694/01bf52fe841a/Beilstein_J_Org_Chem-21-146-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f9b1/11744694/1fbca0e36d56/Beilstein_J_Org_Chem-21-146-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f9b1/11744694/e30d97e83912/Beilstein_J_Org_Chem-21-146-g007.jpg

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