Directed ortho-metalation-nucleophilic acyl substitution strategies in deep eutectic solvents: the organolithium base dictates the chemoselectivity.
Simone GhinatoGiuseppe DilauroFilippo Maria PernaAlejandro Presa SotoMarco BlangettiCristina PrandiPublished in: Chemical communications (Cambridge, England) (2019)
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.
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