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Issue 54, 2019
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Directed ortho-metalation–nucleophilic acyl substitution strategies in deep eutectic solvents: the organolithium base dictates the chemoselectivity

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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.

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

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Supplementary files

Article information


Submitted
21 May 2019
Accepted
30 May 2019
First published
31 May 2019

Chem. Commun., 2019,55, 7741-7744
Article type
Communication

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

S. Ghinato, G. Dilauro, F. M. Perna, V. Capriati, M. Blangetti and C. Prandi, Chem. Commun., 2019, 55, 7741
DOI: 10.1039/C9CC03927A

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