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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