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Molecules 2016, 21(7), 897; doi:10.3390/molecules21070897

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
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)
View Full-Text   |   Download PDF [3762 KB, uploaded 8 July 2016]   |  

Abstract

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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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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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.

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