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Updated: Jun 4, 2025

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
Published on: January 19, 2016
Electrophilic aromatic substitution using fluorinated isoxazolines at the C5 position via C-F bond cleavage
Kazuyuki Sato1, Tomohiro Kuroki1, Haruka Minami1
1Faculty of Pharmaceutical Sciences, Setsunan University 45-1 Nagaotoge-cho Hirakata Osaka 573-0101 Japan sato@pharm.setsunan.ac.jp.
Abstract:
Electrophilic aromatic substitution at the C5 position of isoxazolines and construction of a new quaternary carbon center were achieved in this paper. This is the first report of carbon-carbon (C-C) bond formation onto isoxazoline without compromising the ring structure. Various aromatics including heteroaromatics gave the desired products in good yields, especially aromatics bearing electron-donating groups. The reaction proceeds via the SEAr reaction mechanism, in which carbocation intermediates generated from the fluorinated isoxazolines via C-F bond cleavage reacted with aromatics.
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