Mild, aqueous α-arylation of ketones : towards new diversification tools for halogenated metabolites and drug molecules
- Author
- Enrico Marelli, Yohann Renault, Sunil V Sharma, Steven Nolan (UGent) and Rebecca JM Goss
- Organization
- 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: http://hdl.handle.net/1854/LU-8536744
- Chicago
- 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.
- 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.
- 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.
- MLA
- Marelli, Enrico, Yohann Renault, Sunil V Sharma, et al. “Mild, Aqueous Α-arylation of Ketones : Towards New Diversification Tools for Halogenated Metabolites and Drug Molecules.” CHEMISTRY-A EUROPEAN JOURNAL 23.16 (2017): 3832–3836. Print.
@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},
keyword = {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 \ensuremath{\alpha}-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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