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Access to ortho-Hydroxyphenyl Ketimines via Imine Anion-Mediated Smiles Rearrangement

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journal contribution
posted on 2022-06-07, 14:10 authored by Shunki Jinno, Takahiro Senoo, Keiji Mori
We have achieved a facile access to N-(2-halophenyl)-2-hydroxyphenylimine derivatives via imine anion-mediated Smiles rearrangement. When 2-(2-halophenoxy)­benzonitriles were treated with 1.2–1.4 equiv of organolithium reagents, nucleophilic addition to the nitrile group followed by Smiles rearrangement occurred to give various N-(2-halophenyl)-2-hydroxyphenylimine derivatives, which are sometimes difficult to synthesize by the conventional acid-promoted condensation reaction between carbonyl compounds and aniline derivatives, in good to excellent chemical yields (up to 91%).

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