Potassium-base-mediated defluoroetherification of aryl and heteroaryl fluorides with alkoxyboronic acid pinacol esters under transition-metal-free conditions is reported. This protocol efficiently and safely provides a wide variety of aryl ethers in high yields without using metal catalysts, specific ligands, and harsh conditions to selectively forge C-O bonds via the C-F cleavage. This method can be applied to the late-stage etherification of structurally complex C-fluorides and bioactive alcohols, such as β-estradiol, calciferol, and tocopherol.
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Etherification of Fluoroarenes with Alkoxyboronic Acid Pinacol Esters via C-F Bond Cleavage.
Org Lett
July 2022
Department of Nanopharmaceutical Sciences, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya 466-8555, Japan.
Potassium-base-mediated defluoroetherification of aryl and heteroaryl fluorides with alkoxyboronic acid pinacol esters under transition-metal-free conditions is reported. This protocol efficiently and safely provides a wide variety of aryl ethers in high yields without using metal catalysts, specific ligands, and harsh conditions to selectively forge C-O bonds via the C-F cleavage. This method can be applied to the late-stage etherification of structurally complex C-fluorides and bioactive alcohols, such as β-estradiol, calciferol, and tocopherol.
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