Tickner, Benjamin James, Duckett, Simon orcid.org/0000-0002-9788-6615, Parker, Rachel Roberta et al. (1 more author) (2019) Probing the hydrogenation of vinyl sulfoxides using para-hydrogen. Organometallics. 9b00610. ISSN 0276-7333
Abstract
Vinyl sulfoxides are an important functional group used in a wide range of organic transformations. Here, we use [IrCl(COD)(IMes)] where IMes = 1,3-bis(2,4,6-trimethyl-phenyl)imidazole-2-ylidene and COD = cis,cis-1,5-cyclooctadiene to rapidly hydrogenate phenylvinylsulfoxide. We use ParaHydrogen Induced Hyperpolarization (PHIP) to follow this reaction with [IrCl(H)2(IMes)(S(O)(Ph)(Et))2] dominating in the later stages. Decomposition to form the reduced C-S bond cleaved product [Ir2(H)3(κ2-H)(κ2-SPh)2(IMes)2(S(Et)(Ph)O)] limits turnover. The related product [Ir2(H)4(κ2-S)(IMes)2(S(O)(CH2Ph)2)2] is formed from dibenzylsulfoxide demonstrating the wider utility of this transformation.
Metadata
Item Type: | Article |
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Authors/Creators: |
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Copyright, Publisher and Additional Information: | © 2019 American Chemical Society |
Dates: |
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Institution: | The University of York |
Academic Units: | The University of York > Faculty of Sciences (York) > Chemistry (York) |
Funding Information: | Funder Grant number MEDICAL RESEARCH COUNCIL (MRC) MR/M008991/1 WELLCOME TRUST 098335/Z/12/Z |
Depositing User: | Pure (York) |
Date Deposited: | 07 Nov 2019 15:20 |
Last Modified: | 22 Nov 2024 00:37 |
Published Version: | https://doi.org/10.1021/acs.organomet.9b00610 |
Status: | Published online |
Refereed: | Yes |
Identification Number: | 10.1021/acs.organomet.9b00610 |
Open Archives Initiative ID (OAI ID): | oai:eprints.whiterose.ac.uk:153240 |