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

Author:
Ghinato, Simone, Dilauro, Giuseppe, Perna, Filippo Maria, Capriati, Vito, Blangetti, Marco, Prandi, Cristina
Source:
Chemical communications 2019 v.55 no.54 pp. 7741-7744
ISSN:
1364-548X
Subject:
Lewis bases, chemical reactions, chemoselectivity, choline, solvents
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.
Agid:
6493115