Anionic N-heterocyclic carbenes derived from sydnone imines such as molsidomine. Trapping reactions with selenium, palladium, and gold
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Freese , T , Lücke , A-L , Schmidt , C A S , Polamo , M , Nieger , M , Namyslo , J C & Schmidt , A 2017 , ' Anionic N-heterocyclic carbenes derived from sydnone imines such as molsidomine. Trapping reactions with selenium, palladium, and gold ' , Tetrahedron , vol. 73 , no. 36 , pp. 5350-5357 . https://doi.org/10.1016/j.tet.2017.07.032
| Title: | Anionic N-heterocyclic carbenes derived from sydnone imines such as molsidomine. Trapping reactions with selenium, palladium, and gold |
| Author: | Freese, Tyll; Lücke, Ana-Luiza; Schmidt, Catharina A. S.; Polamo, Mika; Nieger, Martin; Namyslo, Jan C.; Schmidt, Andreas |
| Contributor organization: | Department of Chemistry Department |
| Date: | 2017-09-07 |
| Language: | eng |
| Number of pages: | 8 |
| Belongs to series: | Tetrahedron |
| ISSN: | 0040-4020 |
| DOI: | https://doi.org/10.1016/j.tet.2017.07.032 |
| URI: | http://hdl.handle.net/10138/309235 |
| Abstract: | The sydnone imines Molsidomine and 5-(benzoylimino)-3-(2-methoxyphenyl)-1,2,3-oxadiazolium-2-ide gave anionic N-heterocyclic carbenes on deprotonation at C4 which were trapped as methylated selenium adducts, gold complexes (X-ray analysis) as well as palladium complexes (X-ray analysis). The C-13 NMR resonance frequencies of the carbene carbon atom are extremely shifted upfield and appear at delta = 142.1 ppm (Molsidomine carbene) and delta = 159.8 ppm (sydnone imine carbene). The Pd complexes were applied as catalysts in Suzuki-Miyaura and Sonogashira-Hagihara cross-coupling reactions. (C) 2017 Elsevier Ltd. All rights reserved. |
| Subject: |
Mesoionic compound
Carbon(0) Carbene Suzuki-Miyaura reactions Sonogashira-Hagihara reactions MESOMERIC BETAINES HEILMITTELCHEMISCHE STUDIEN COORDINATION CHEMISTRY COUPLING REACTIONS UBER SYDNONIMINE METAL-COMPLEXES BORANE ADDUCTS AMINO-ACIDS LIGANDS IMIDAZOLIUM 116 Chemical sciences |
| Peer reviewed: | Yes |
| Rights: | cc_by_nc_nd |
| Usage restriction: | openAccess |
| Self-archived version: | acceptedVersion |
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