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

Molecules

Nicola Della Ca’¹  Christian Pomelli²  Cinzia Chiappe²  Ida Ziccarelli³  Asif Maner³  Bartolo Gabriele³  Raffaella Mancuso³  Lucia Veltri³ 

[1] Department of Chemistry, University of Parma, Parco Area delle Scienze 17/A, 43124 Parma, Italy;Department of Pharmacy, University of Pisa, Via Bonanno 33, 56126 Pisa, Italy;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;

关键词: carbonylation;    cascade catalysis;    oxazolidinones;    palladium;   

DOI  :  10.3390/molecules21070897

来源: DOAJ

【 摘 要 】

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.

【 授权许可】

Unknown