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Asymmetric transfer hydrogenation of aryl heteroaryl ketones using Noyori‐Ikariya catalysts
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Wills, Martin, Zheng, Ye, Martinez-Acosta, Jaime, Khimji, Mohammed, Barbosa, Luiz Claudio and Clarkson, Guy J. (2021) Asymmetric transfer hydrogenation of aryl heteroaryl ketones using Noyori‐Ikariya catalysts. ChemCatChem, 13 (20). pp. 4384-4391. doi:10.1002/cctc.202101027 ISSN 1867-3880.
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WRAP-Asymmetric-transfer-hydrogenation-heteroaryl-ketones-Noyori-Ikariya-catalysts-2021.pdf - Accepted Version - Requires a PDF viewer. Download (1289Kb) | Preview |
Official URL: https://doi.org/10.1002/cctc.202101027
Abstract
A range of ketones flanked by a combination of an aromatic and a heterocyclic ring (furan, thiophene, N -methylimidazole) were reduced under asymmetric transfer hydrogenation (ATH) conditions. Using a range of [(arene)Ru(TsDPEN)Cl] precatalysts, including tethered derivatives, the reduction enantioselectivity was high (up to 99% ee) in cases where the aromatic ring contained an ortho -substituent. The enantioselectivity is influenced by a combination of steric and electronic factors which for the furan and thiophene series, follow literature precedents. In the case of the N -methylimidazole-containing ketones, an unexpected switch in enantioselectivity took place upon variation of the opposing aromatic group. Pyrrole- containing ketones were resistant to reduction. This study demonstrates the asymmetric transfer hydrogenation (ATH) of a range of hindered heterocyclic ketones, in high conversion and ee, using Noyori-Ikariya catalysts.
Item Type: | Journal Article | |||||||||||||||
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Subjects: | Q Science > QD Chemistry | |||||||||||||||
Divisions: | Faculty of Science, Engineering and Medicine > Science > Chemistry | |||||||||||||||
SWORD Depositor: | Library Publications Router | |||||||||||||||
Library of Congress Subject Headings (LCSH): | Hydrogenation, Heterocyclic compounds, Ketones, Chemistry, Organic, Catalysis | |||||||||||||||
Journal or Publication Title: | ChemCatChem | |||||||||||||||
Publisher: | Wiley - V C H Verlag GmbH & Co. KGaA | |||||||||||||||
ISSN: | 1867-3880 | |||||||||||||||
Official Date: | 19 October 2021 | |||||||||||||||
Dates: |
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Volume: | 13 | |||||||||||||||
Number: | 20 | |||||||||||||||
Page Range: | pp. 4384-4391 | |||||||||||||||
DOI: | 10.1002/cctc.202101027 | |||||||||||||||
Status: | Peer Reviewed | |||||||||||||||
Publication Status: | Published | |||||||||||||||
Reuse Statement (publisher, data, author rights): | "This is the peer reviewed version of the following article: Wills, M., Zheng, Y., Martinez-Acosta, J., Khimji, M., Barbosa, L.C. and Clarkson, G. (2021), Asymmetric transfer hydrogenation of aryl heteroaryl ketones using Noyori-Ikariya catalysts. ChemCatChem. Accepted Author Manuscript., which has been published in final form at https://doi.org/10.1002/cctc.202101027. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Use of Self-Archived Versions." | |||||||||||||||
Access rights to Published version: | Restricted or Subscription Access | |||||||||||||||
Date of first compliant deposit: | 16 August 2021 | |||||||||||||||
Date of first compliant Open Access: | 24 July 2022 | |||||||||||||||
RIOXX Funder/Project Grant: |
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