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Expedient syntheses of the N-heterocyclic carbene precursor imidazolium salts IPr·HCl, IMes·HCl and IXy·HCl
The 1,3-diaryl-imidazolium chlorides IPr·HCl (aryl = 2,6-diisopropylphenyl), IMes·HCl (aryl = 2,4,6-trimethylphenyl) and IXy·HCl (aryl = 2,6-dimethylphenyl), precursors to widely used N-heterocyclic carbene (NHC) ligands and catalysts, were prepared in high yields (81%, 69% and 89%, respectively) by...
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Formato: | Texto |
Lenguaje: | English |
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Beilstein-Institut
2007
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Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2151073/ https://www.ncbi.nlm.nih.gov/pubmed/17725838 http://dx.doi.org/10.1186/1860-5397-3-22 |
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author | Hintermann, Lukas |
author_facet | Hintermann, Lukas |
author_sort | Hintermann, Lukas |
collection | PubMed |
description | The 1,3-diaryl-imidazolium chlorides IPr·HCl (aryl = 2,6-diisopropylphenyl), IMes·HCl (aryl = 2,4,6-trimethylphenyl) and IXy·HCl (aryl = 2,6-dimethylphenyl), precursors to widely used N-heterocyclic carbene (NHC) ligands and catalysts, were prepared in high yields (81%, 69% and 89%, respectively) by the reaction of 1,4-diaryl-1, 4-diazabutadienes, paraformaldehyde and chlorotrimethylsilane in dilute ethyl acetate solution. A reaction mechanism involving a 1,5-dipolar electrocyclization is proposed. |
format | Text |
id | pubmed-2151073 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2007 |
publisher | Beilstein-Institut |
record_format | MEDLINE/PubMed |
spelling | pubmed-21510732007-12-21 Expedient syntheses of the N-heterocyclic carbene precursor imidazolium salts IPr·HCl, IMes·HCl and IXy·HCl Hintermann, Lukas Beilstein J Org Chem Full Research Paper The 1,3-diaryl-imidazolium chlorides IPr·HCl (aryl = 2,6-diisopropylphenyl), IMes·HCl (aryl = 2,4,6-trimethylphenyl) and IXy·HCl (aryl = 2,6-dimethylphenyl), precursors to widely used N-heterocyclic carbene (NHC) ligands and catalysts, were prepared in high yields (81%, 69% and 89%, respectively) by the reaction of 1,4-diaryl-1, 4-diazabutadienes, paraformaldehyde and chlorotrimethylsilane in dilute ethyl acetate solution. A reaction mechanism involving a 1,5-dipolar electrocyclization is proposed. Beilstein-Institut 2007-08-28 /pmc/articles/PMC2151073/ /pubmed/17725838 http://dx.doi.org/10.1186/1860-5397-3-22 Text en Copyright © 2007, Hintermann https://creativecommons.org/licenses/by/2.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms) |
spellingShingle | Full Research Paper Hintermann, Lukas Expedient syntheses of the N-heterocyclic carbene precursor imidazolium salts IPr·HCl, IMes·HCl and IXy·HCl |
title | Expedient syntheses of the N-heterocyclic carbene precursor imidazolium salts IPr·HCl, IMes·HCl and IXy·HCl |
title_full | Expedient syntheses of the N-heterocyclic carbene precursor imidazolium salts IPr·HCl, IMes·HCl and IXy·HCl |
title_fullStr | Expedient syntheses of the N-heterocyclic carbene precursor imidazolium salts IPr·HCl, IMes·HCl and IXy·HCl |
title_full_unstemmed | Expedient syntheses of the N-heterocyclic carbene precursor imidazolium salts IPr·HCl, IMes·HCl and IXy·HCl |
title_short | Expedient syntheses of the N-heterocyclic carbene precursor imidazolium salts IPr·HCl, IMes·HCl and IXy·HCl |
title_sort | expedient syntheses of the n-heterocyclic carbene precursor imidazolium salts ipr·hcl, imes·hcl and ixy·hcl |
topic | Full Research Paper |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2151073/ https://www.ncbi.nlm.nih.gov/pubmed/17725838 http://dx.doi.org/10.1186/1860-5397-3-22 |
work_keys_str_mv | AT hintermannlukas expedientsynthesesofthenheterocycliccarbeneprecursorimidazoliumsaltsiprhclimeshclandixyhcl |