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Mild, aqueous α-arylation of ketones: towards new diversification tools for halogenated metabolites and drug molecules

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Author(s)

Enrico Marelli, Yohann Renault, Sunil V. Sharma, Steven P. Nolan, Rebecca J. M. Goss

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Abstract

The palladium-catalyzed aqueous α-arylation of ketones was developed and tested for a large variety of reaction partners. These mild conditions enabled the coupling of aryl/ alkyl-ketones with N-protected halotryptophans, heterocyclic haloarenes, and challenging base-sensitive compounds. The synthetic potential of this new methodology for the diversification of complex bioactive molecules was exemplified by derivatising prochlorperazine. The methodology is mild, aqueous and flexible, representing a means of functionalizing a wide range of halo-aromatics and therefore has the potential to be extended to complex molecule diversification.
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Original languageEnglish
Pages (from-to)3832-3836
Number of pages5
JournalChemistry - A European Journal
Volume23
Issue number16
Early online date6 Mar 2017
DOIs
StatePublished - 17 Mar 2017

    Research areas

  • Palladium, Aqueous coupling, Halogenated compounds, Ketone arylation, Amino acids

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