Nickel-Catalyzed Cross-Coupling of 2-Fluorobenzofurans with Arylboronic Acids via Aromatic C–F Bond Activation

Submitting author affiliation:
Sagami Chemical Research Institute, Ayase, Japan

Beilstein Arch. 2024, 202463. https://doi.org/10.3762/bxiv.2024.63.v1

Published 04 Nov 2024

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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 and zero-valent nickel species. This protocol facilitates orthogonal coupling reactions of aromatic C–F and C–Br bonds with arylboronic acids.

Keywords: C–F Bond Activation; Nickel; Cross-Coupling; Benzofuran; Arylboronic Acid

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Fujita, T.; Yabuki, H.; Morioka, R.; Fuchibe, K.; Ichikawa, J. Beilstein Arch. 2024, 202463. doi:10.3762/bxiv.2024.63.v1

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