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

Enrico Marelli, Yohann Renault, Sunil V Sharma, Steven Nolan (UGent) and Rebecca JM Goss
(2017) CHEMISTRY-A EUROPEAN JOURNAL. 23(16). p.3832-3836
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Abstract
The palladium-catalysed aqueous -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.
Keywords
amino acids, aqueous coupling, halogenated compounds, ketone arylation, palladium, CATALYZED ALPHA-ARYLATION, CROSS-COUPLING REACTIONS, ARYL CHLORIDES, REDUCTIVE ELIMINATION, PALLADIUM CATALYSTS, BOND FORMATION, AMINO-ACIDS, DERIVATIVES, COMPLEXES, FUNCTIONALIZATION

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Citation

Please use this url to cite or link to this publication:

MLA
Marelli, Enrico, et al. “Mild, Aqueous α-Arylation of Ketones : Towards New Diversification Tools for Halogenated Metabolites and Drug Molecules.” CHEMISTRY-A EUROPEAN JOURNAL, vol. 23, no. 16, 2017, pp. 3832–36.
APA
Marelli, E., Renault, Y., Sharma, S. V., Nolan, S., & Goss, R. J. (2017). Mild, aqueous α-arylation of ketones : towards new diversification tools for halogenated metabolites and drug molecules. CHEMISTRY-A EUROPEAN JOURNAL, 23(16), 3832–3836.
Chicago author-date
Marelli, Enrico, Yohann Renault, Sunil V Sharma, Steven Nolan, and Rebecca JM Goss. 2017. “Mild, Aqueous α-Arylation of Ketones : Towards New Diversification Tools for Halogenated Metabolites and Drug Molecules.” CHEMISTRY-A EUROPEAN JOURNAL 23 (16): 3832–36.
Chicago author-date (all authors)
Marelli, Enrico, Yohann Renault, Sunil V Sharma, Steven Nolan, and Rebecca JM Goss. 2017. “Mild, Aqueous α-Arylation of Ketones : Towards New Diversification Tools for Halogenated Metabolites and Drug Molecules.” CHEMISTRY-A EUROPEAN JOURNAL 23 (16): 3832–3836.
Vancouver
1.
Marelli E, Renault Y, Sharma SV, Nolan S, Goss RJ. Mild, aqueous α-arylation of ketones : towards new diversification tools for halogenated metabolites and drug molecules. CHEMISTRY-A EUROPEAN JOURNAL. 2017;23(16):3832–6.
IEEE
[1]
E. Marelli, Y. Renault, S. V. Sharma, S. Nolan, and R. J. Goss, “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, 2017.
@article{8536744,
  abstract     = {The palladium-catalysed aqueous -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.},
  author       = {Marelli, Enrico and Renault, Yohann and Sharma, Sunil V and Nolan, Steven and Goss, Rebecca JM},
  issn         = {0947-6539},
  journal      = {CHEMISTRY-A EUROPEAN JOURNAL},
  keywords     = {amino acids,aqueous coupling,halogenated compounds,ketone arylation,palladium,CATALYZED ALPHA-ARYLATION,CROSS-COUPLING REACTIONS,ARYL CHLORIDES,REDUCTIVE ELIMINATION,PALLADIUM CATALYSTS,BOND FORMATION,AMINO-ACIDS,DERIVATIVES,COMPLEXES,FUNCTIONALIZATION},
  language     = {eng},
  number       = {16},
  pages        = {3832--3836},
  title        = {Mild, aqueous α-arylation of ketones : towards new diversification tools for halogenated metabolites and drug molecules},
  url          = {http://dx.doi.org/10.1002/chem.201700680},
  volume       = {23},
  year         = {2017},
}
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