Synthesis and chiroptical properties of organometallic complexes of helicenic N-heterocyclic carbenes
© 2019 Wiley Periodicals, Inc..
Novel [4, 6]helicenes (4a,b) bearing a fused imidazolium unit have been prepared from [4, 6]helicene-2,3-di-n-propyl-amines 3a,b. The in situ formation of N-heterocyclic carbene (NHC) derivatives followed by their complexation to iridium(I) or rhodium(I) gave access to complexes 1a, 1'a, and 1b, containing mono-coordinated helicene-NHC, chloro and COD (COD = 1,5-cyclooctadiene) ligands. Ir and Rh complexes 1a and 1'a were characterized by X-ray crystallography. HPLC and NMR analyses showed that Ir(I) complex 1b existed as a mixture of two diastereomeric complexes corresponding to enantiomeric pairs M-(-)/P-(+)-1b1 and M-(-)/P-(+)-1b2 which differ by the position of COD through space. The chiroptical properties (electronic circular dichroism and optical rotation) of the four stereoisomers were measured. These complexes were also tested as catalysts in a transfer hydrogenation reaction.
| Medienart: |
E-Artikel |
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| Erscheinungsjahr: |
2019 |
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| Erschienen: |
2019 |
| Enthalten in: |
Zur Gesamtaufnahme - volume:31 |
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| Enthalten in: |
Chirality - 31(2019), 12 vom: 02. Dez., Seite 1005-1013 |
| Sprache: |
Englisch |
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| Beteiligte Personen: |
Hafedh, Nesrine [VerfasserIn] |
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| Links: |
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| Themen: |
Chiroptical properties |
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| Anmerkungen: |
Date Completed 26.11.2019 Date Revised 08.01.2020 published: Print-Electronic Citation Status PubMed-not-MEDLINE |
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| doi: |
10.1002/chir.23143 |
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| funding: |
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| Förderinstitution / Projekttitel: |
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| PPN (Katalog-ID): |
NLM302749179 |
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| 500 | |a published: Print-Electronic | ||
| 500 | |a Citation Status PubMed-not-MEDLINE | ||
| 520 | |a © 2019 Wiley Periodicals, Inc. | ||
| 520 | |a Novel [4, 6]helicenes (4a,b) bearing a fused imidazolium unit have been prepared from [4, 6]helicene-2,3-di-n-propyl-amines 3a,b. The in situ formation of N-heterocyclic carbene (NHC) derivatives followed by their complexation to iridium(I) or rhodium(I) gave access to complexes 1a, 1'a, and 1b, containing mono-coordinated helicene-NHC, chloro and COD (COD = 1,5-cyclooctadiene) ligands. Ir and Rh complexes 1a and 1'a were characterized by X-ray crystallography. HPLC and NMR analyses showed that Ir(I) complex 1b existed as a mixture of two diastereomeric complexes corresponding to enantiomeric pairs M-(-)/P-(+)-1b1 and M-(-)/P-(+)-1b2 which differ by the position of COD through space. The chiroptical properties (electronic circular dichroism and optical rotation) of the four stereoisomers were measured. These complexes were also tested as catalysts in a transfer hydrogenation reaction | ||
| 650 | 4 | |a Journal Article | |
| 650 | 4 | |a Research Support, Non-U.S. Gov't | |
| 650 | 4 | |a N-heterocyclic carbenes | |
| 650 | 4 | |a chiroptical properties | |
| 650 | 4 | |a helicenes | |
| 650 | 4 | |a iridium | |
| 650 | 4 | |a transfer hydrogenation | |
| 700 | 1 | |a Favereau, Ludovic |e verfasserin |4 aut | |
| 700 | 1 | |a Caytan, Elsa |e verfasserin |4 aut | |
| 700 | 1 | |a Roisnel, Thierry |e verfasserin |4 aut | |
| 700 | 1 | |a Jean, Marion |e verfasserin |4 aut | |
| 700 | 1 | |a Vanthuyne, Nicolas |e verfasserin |4 aut | |
| 700 | 1 | |a Aloui, Faouzi |e verfasserin |4 aut | |
| 700 | 1 | |a Crassous, Jeanne |e verfasserin |4 aut | |
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