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Dirhodium Coordination Polymers for Asymmetric Cyclopropanation of Diazooxindoles with Olefins: Synthesis and Spectroscopic Analysis

Li, Zhenzhong ; Rösler, Lorenz ; Herr, Kevin ; Brodrecht, Martin ; Breitzke, Hergen ; Hofmann, Kathrin ; Limbach, Hans‐Heinrich ; Gutmann, Torsten ; Buntkowsky, Gerd (2020)
Dirhodium Coordination Polymers for Asymmetric Cyclopropanation of Diazooxindoles with Olefins: Synthesis and Spectroscopic Analysis.
In: ChemPlusChem, 85 (8)
doi: 10.1002/cplu.202000421
Article, Bibliographie

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Abstract

A facile approach is reported for the preparation of dirhodium coordination polymers [Rh₂(L1)₂]n (Rh₂-L1) and [Rh₂(L2)₂]n (Rh₂-L2; L1=N,N’-(pyromellitoyl)-bis-L-phenylalanine diacid anion, L2=bis-N,N’-(L-phenylalanyl) naphthalene-1,4,5,8-tetracarboxylate diimide) from chiral dicarboxylic acids by ligand exchange. Multiple techniques including FTIR, XPS, and ¹H→¹³C CP MAS NMR spectroscopy reveal the formation of the coordination polymers. ¹⁹F MAS NMR was utilized to investigate the remaining TFA groups in the obtained coordination polymers, and demonstrated near-quantitative ligand exchange. DR-UV-vis and XPS confirm the oxidation state of the Rh center and that the Rh-single bond in the dirhodium node is maintained in the synthesis of Rh₂-L1 and Rh₂-L2. Both coordination polymers exhibit excellent catalytic performance in the asymmetric cyclopropanation reaction between styrene and diazooxindole. The catalysts can be easily recycled and reused without significant reduction in their catalytic efficiency.

Item Type: Article
Erschienen: 2020
Creators: Li, Zhenzhong ; Rösler, Lorenz ; Herr, Kevin ; Brodrecht, Martin ; Breitzke, Hergen ; Hofmann, Kathrin ; Limbach, Hans‐Heinrich ; Gutmann, Torsten ; Buntkowsky, Gerd
Type of entry: Bibliographie
Title: Dirhodium Coordination Polymers for Asymmetric Cyclopropanation of Diazooxindoles with Olefins: Synthesis and Spectroscopic Analysis
Language: English
Date: 2020
Publisher: Wiley-VCH
Journal or Publication Title: ChemPlusChem
Volume of the journal: 85
Issue Number: 8
DOI: 10.1002/cplu.202000421
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Abstract:

A facile approach is reported for the preparation of dirhodium coordination polymers [Rh₂(L1)₂]n (Rh₂-L1) and [Rh₂(L2)₂]n (Rh₂-L2; L1=N,N’-(pyromellitoyl)-bis-L-phenylalanine diacid anion, L2=bis-N,N’-(L-phenylalanyl) naphthalene-1,4,5,8-tetracarboxylate diimide) from chiral dicarboxylic acids by ligand exchange. Multiple techniques including FTIR, XPS, and ¹H→¹³C CP MAS NMR spectroscopy reveal the formation of the coordination polymers. ¹⁹F MAS NMR was utilized to investigate the remaining TFA groups in the obtained coordination polymers, and demonstrated near-quantitative ligand exchange. DR-UV-vis and XPS confirm the oxidation state of the Rh center and that the Rh-single bond in the dirhodium node is maintained in the synthesis of Rh₂-L1 and Rh₂-L2. Both coordination polymers exhibit excellent catalytic performance in the asymmetric cyclopropanation reaction between styrene and diazooxindole. The catalysts can be easily recycled and reused without significant reduction in their catalytic efficiency.

Classification DDC: 500 Science and mathematics > 540 Chemistry
Divisions: 07 Department of Chemistry
07 Department of Chemistry > Eduard Zintl-Institut
07 Department of Chemistry > Eduard Zintl-Institut > Physical Chemistry
Date Deposited: 02 Aug 2024 12:37
Last Modified: 02 Aug 2024 12:37
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