Mild, aqueous α-arylation of ketones : towards new diversification tools for halogenated metabolites and drug molecules
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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.
Marelli , E , Renault , Y , Sharma , S V , Nolan , S P & Goss , R J M 2017 , ' Mild, aqueous α-arylation of ketones : towards new diversification tools for halogenated metabolites and drug molecules ' Chemistry - A European Journal , vol 23 , no. 16 , pp. 3832-3836 . DOI: 10.1002/chem.201700680
Chemistry - A European Journal
© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim. This work has been made available online in accordance with the publisher’s policies. This is the author created, accepted version manuscript following peer review and may differ slightly from the final published version. The final published version of this work is available at: https://doi.org/10.1002/chem.201700680
The authors thank the European Research Council (FP7/2007-2013/ERC grant agreement no 614779 to RJMG) and (FP7 2009-2014/ERC agreement no 227817 to SPN) for generous funding.
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