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Probing the Hydrogenation of Vinyl Sulfoxides Using para-Hydrogen
[Image: see text] 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 us...
Autores principales: | , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
American Chemical
Society
2019
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Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6880776/ https://www.ncbi.nlm.nih.gov/pubmed/31787798 http://dx.doi.org/10.1021/acs.organomet.9b00610 |
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author | Tickner, Ben J. Parker, Rachel R. Whitwood, Adrian C. Duckett, Simon B. |
author_facet | Tickner, Ben J. Parker, Rachel R. Whitwood, Adrian C. Duckett, Simon B. |
author_sort | Tickner, Ben J. |
collection | PubMed |
description | [Image: see text] 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 para-hydrogen-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 cleavage product [Ir(2)(H)(3)(κ(2)-H)(κ(2)-SPh)(2)(IMes)(2)(S(Et)(Ph)O)] limits turnover. The related product [Ir(2)(H)(4)(κ(2)-S)(IMes)(2)(S(O)(CH(2)Ph)(2))(2)] is formed from dibenzylsulfoxide, demonstrating the wider utility of this transformation. |
format | Online Article Text |
id | pubmed-6880776 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2019 |
publisher | American Chemical
Society |
record_format | MEDLINE/PubMed |
spelling | pubmed-68807762019-11-29 Probing the Hydrogenation of Vinyl Sulfoxides Using para-Hydrogen Tickner, Ben J. Parker, Rachel R. Whitwood, Adrian C. Duckett, Simon B. Organometallics [Image: see text] 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 para-hydrogen-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 cleavage product [Ir(2)(H)(3)(κ(2)-H)(κ(2)-SPh)(2)(IMes)(2)(S(Et)(Ph)O)] limits turnover. The related product [Ir(2)(H)(4)(κ(2)-S)(IMes)(2)(S(O)(CH(2)Ph)(2))(2)] is formed from dibenzylsulfoxide, demonstrating the wider utility of this transformation. American Chemical Society 2019-11-14 2019-11-25 /pmc/articles/PMC6880776/ /pubmed/31787798 http://dx.doi.org/10.1021/acs.organomet.9b00610 Text en Copyright © 2019 American Chemical Society This is an open access article published under a Creative Commons Attribution (CC-BY) License (http://pubs.acs.org/page/policy/authorchoice_ccby_termsofuse.html) , which permits unrestricted use, distribution and reproduction in any medium, provided the author and source are cited. |
spellingShingle | Tickner, Ben J. Parker, Rachel R. Whitwood, Adrian C. Duckett, Simon B. Probing the Hydrogenation of Vinyl Sulfoxides Using para-Hydrogen |
title | Probing the
Hydrogenation of Vinyl Sulfoxides Using para-Hydrogen |
title_full | Probing the
Hydrogenation of Vinyl Sulfoxides Using para-Hydrogen |
title_fullStr | Probing the
Hydrogenation of Vinyl Sulfoxides Using para-Hydrogen |
title_full_unstemmed | Probing the
Hydrogenation of Vinyl Sulfoxides Using para-Hydrogen |
title_short | Probing the
Hydrogenation of Vinyl Sulfoxides Using para-Hydrogen |
title_sort | probing the
hydrogenation of vinyl sulfoxides using para-hydrogen |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6880776/ https://www.ncbi.nlm.nih.gov/pubmed/31787798 http://dx.doi.org/10.1021/acs.organomet.9b00610 |
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