Auto-Tandem Catalysis in Ionic Liquids: Synthesis of 2-Oxazolidinones by Palladium-Catalyzed Oxidative Carbonylation of Propargylic Amines in EmimEtSO(4)

作者：Mancuso Raffaella^*; Maner Asif; Ziccarelli Ida; Pomelli Christian; Chiappe Cinzia; Della Ca' Nicola; Veltri Lucia; Gabriele Bartolo^*

来源：Molecules, 2016, 21(7): 897.

DOI：10.3390/molecules21070897

• carbonylation
• cascade catalysis
• oxazolidinones
• palladium

A convenient carbonylative approach to 2-oxazolidinone derivatives carried out using an ionic liquid (1-ethyl-3-methylimidazolium ethyl sulfate, EmimEtSO(4)) 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.

• 出版日期2016-7