Ortho-Selective amination of arene carboxylic acids via rearrangement of acyl O-hydroxylamines.

ABSTRACT: Direct amination of arene C-H bonds is an attractive disconnection to form aniline-derived building blocks. This transformation presents significant practical challenges; classical methods for ortho-selective amination require strongly acidic or forcing conditions, while contemporary catalytic processes often require bespoke directing groups and/or precious metal catalysis. We report a mild and procedurally straightforward ortho-selective amination of arene carboxylic acids, arising from a facile rearrangement of acyl O-hydroxylamines without requiring precious metal catalysts. A broad scope of benzoic acid substrates are compatible and the reaction can be applied to longer chain arene carboxylic acids. Mechanistic studies probe the specific requirement for trifluoroac

SUBMITTER: Gillespie JE 

PROVIDER: S-EPMC10530477 | biostudies-literature | 2023 Sep

REPOSITORIES: biostudies-literature