Directed ortho-metalation-nucleophilic acyl substitution strategies in deep eutectic solvents: the organolithium base dictates the chemoselectivity

Chem Commun (Camb). 2019 Jul 11;55(54):7741-7744. doi: 10.1039/c9cc03927a. Epub 2019 Jun 6.

Abstract

Directed ortho metalation (DoM) or nucleophilic acyl substitution (SNAc) can be efficiently programmed on the same aromatic carboxylic acid amide, in a choline chloride-based eutectic mixture, by simply switching the nature of the organolithium reagent. Telescoped, one-pot ortho-lithiation/Suzuki-Miyaura cross-couplings have also been demonstrated for the first time in Deep Eutectic Solvents.