title: Auto-Tandem Catalysis in Ionic Liquids: Synthesis of 2-Oxazolidinones by Palladium-Catalyzed Oxidative Carbonylation of Propargylic Amines in EmimEtSO₄.
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.
authors.affiliation: 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. raffaella.mancuso@unical.it.
authors.forename: Raffaella
authors.initials: R
authors.lastname: Mancuso
authors.affiliation: 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. asifncl@gmail.com.
authors.forename: Asif
authors.initials: A
authors.lastname: Maner
authors.affiliation: 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. idaziccarelli@gmail.com.
authors.forename: Ida
authors.initials: I
authors.lastname: Ziccarelli
authors.affiliation: Department of Pharmacy, University of Pisa, Via Bonanno 33, 56126 Pisa, Italy. christian.pomelli@gmail.com.
authors.forename: Christian
authors.initials: C
authors.lastname: Pomelli
authors.affiliation: Department of Pharmacy, University of Pisa, Via Bonanno 33, 56126 Pisa, Italy. cinzia.chiappe@farm.unipi.it.
authors.forename: Cinzia
authors.initials: C
authors.lastname: Chiappe
authors.affiliation: Department of Chemistry, University of Parma, Parco Area delle Scienze 17/A, 43124 Parma, Italy. nicola.dellaca@unipr.it.
authors.forename: Nicola
authors.initials: N
authors.lastname: Della Ca'
authors.affiliation: 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. lucia.veltri@unical.it.
authors.forename: Lucia
authors.initials: L
authors.lastname: Veltri
authors.affiliation: 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. bartolo.gabriele@unical.it.
authors.forename: Bartolo
authors.initials: B
authors.lastname: Gabriele
mesh_terms: D000081:Acetamides / Q000138:chemical synthesis; D002384:Catalysis; D003500:Cyclization; D007093:Imidazoles / Q000737:chemistry*; D052578:Ionic Liquids / Q000737:chemistry*; D023303:Oxazolidinones / Q000138:chemical synthesis*; D010084:Oxidation-Reduction; D010165:Palladium / Q000737:chemistry*; D010293:Pargyline / Q000031:analogs & derivatives* / Q000737:chemistry; D011437:Propylamines / Q000737:chemistry*
chemical_list: D000081:Acetamides; D007093:Imidazoles; D052578:Ionic Liquids; D023303:Oxazolidinones; D011437:Propylamines; C009054:propargylamine; D010165:Palladium; D010293:Pargyline; C518739:1-ethyl-3-methylimidazolium
keywords: carbonylation; cascade catalysis; oxazolidinones; palladium