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

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Marelli_2017_CEJ_HalogenatedMetabolites_AAM.pdf (1.361Mb)
Date
17/03/2017
Author
Marelli, Enrico
Renault, Yohann
Sharma, Sunil V.
Nolan, Steven P.
Goss, Rebecca J. M.
Keywords
Palladium
Aqueous coupling
Halogenated compounds
Ketone arylation
Amino acids
QD Chemistry
NDAS
Metadata
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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.
Citation
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 . https://doi.org/10.1002/chem.201700680
Publication
Chemistry - A European Journal
Status
Peer reviewed
DOI
https://doi.org/10.1002/chem.201700680
ISSN
1521-3765
Type
Journal article
Rights
© 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
Description
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.
Collections
  • University of St Andrews Research
URI
http://hdl.handle.net/10023/12864

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