Update of the Imine-Anion-Mediated Smiles Rearrangement: Application to Migration of Electron-Neutral/Rich Aromatic Groups

Synlett DOI: 10.1055/a-2219-5767 We have revisited the imine-anion-mediated Smiles rearrangement for the synthesis of ortho-hydroxyphenyl arylketimines. Detailed examinations revealed that migration of various aromatic groups, previously considered to be unsuited to SNAr-type reactions, such as electron-rich or sterically hindered aromatic groups, can be accomplished by introducing bulky 9-anthryllithium as a nucleophile. Among the aromatic groups examined, naphthyl groups (1- and 2-naphthyl groups) exhibited an excellent performance, and their migration ability was well illustrated by the reaction with less bulky nucleophiles. [...] Georg Thieme Verlag KG Rüdigerstraße 14, 70469 Stuttgart, GermanyArticle in Thieme eJournals: Table of contents  |  Abstract  |  Full text

Source: Synlett - January 4, 2024 Category: Chemistry Authors: Jinno, Shunki Kawasaki-Takasuka, Tomoko Mori, Keiji Tags: letter Source Type: research