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Article

Auto-Tandem Catalysis in Ionic Liquids: Synthesis of 2-Oxazolidinones by Palladium-Catalyzed Oxidative Carbonylation of Propargylic Amines in EmimEtSO4

1
Laboratory of Industrial and Synthetic Organic Chemistry (LISOC), Department of Chemistry and Chemical Technologies, University of Calabria, Via Pietro Bucci 12/C, 87036 Arcavacata di Rende (CS), Italy
2
Department of Pharmacy, University of Pisa, Via Bonanno 33, 56126 Pisa, Italy
3
Department of Chemistry, University of Parma, Parco Area delle Scienze 17/A, 43124 Parma, Italy
*
Authors to whom correspondence should be addressed.
Academic Editor: Derek J. McPhee
Molecules 2016, 21(7), 897; https://doi.org/10.3390/molecules21070897
Received: 16 June 2016 / Revised: 1 July 2016 / Accepted: 5 July 2016 / Published: 8 July 2016
(This article belongs to the Special Issue Cascade Catalysis)
A convenient carbonylative approach to 2-oxazolidinone derivatives carried out using an ionic liquid (1-ethyl-3-methylimidazolium ethyl sulfate, EmimEtSO4) as the solvent is presented. It is based on the sequential concatenation of two catalytic cycles, both catalyzed by the same metal species (auto-tandem catalysis): the first cycle corresponds to the oxidative monoaminocarbonylation of the triple bond of propargylic amines to give the corresponding 2-ynamide intermediates, while the second one involves the cyclocarbonylation of the latter to yield 2-(2-oxooxazolidin-5-ylidene)-acetamides. Reactions are carried out using a simple catalytic system consisting of PdI2 in conjunction with an excess of KI, and the catalyst/solvent system could be recycled several times without appreciable loss of activity after extraction of the organic product with Et2O. View Full-Text
Keywords: carbonylation; cascade catalysis; oxazolidinones; palladium carbonylation; cascade catalysis; oxazolidinones; palladium
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MDPI and ACS Style

Mancuso, R.; Maner, A.; Ziccarelli, I.; Pomelli, C.; Chiappe, C.; Della Ca’, N.; Veltri, L.; Gabriele, B. Auto-Tandem Catalysis in Ionic Liquids: Synthesis of 2-Oxazolidinones by Palladium-Catalyzed Oxidative Carbonylation of Propargylic Amines in EmimEtSO4. Molecules 2016, 21, 897. https://doi.org/10.3390/molecules21070897

AMA Style

Mancuso R, Maner A, Ziccarelli I, Pomelli C, Chiappe C, Della Ca’ N, Veltri L, Gabriele B. Auto-Tandem Catalysis in Ionic Liquids: Synthesis of 2-Oxazolidinones by Palladium-Catalyzed Oxidative Carbonylation of Propargylic Amines in EmimEtSO4. Molecules. 2016; 21(7):897. https://doi.org/10.3390/molecules21070897

Chicago/Turabian Style

Mancuso, Raffaella, Asif Maner, Ida Ziccarelli, Christian Pomelli, Cinzia Chiappe, Nicola Della Ca’, Lucia Veltri, and Bartolo Gabriele. 2016. "Auto-Tandem Catalysis in Ionic Liquids: Synthesis of 2-Oxazolidinones by Palladium-Catalyzed Oxidative Carbonylation of Propargylic Amines in EmimEtSO4" Molecules 21, no. 7: 897. https://doi.org/10.3390/molecules21070897

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