4.6 Article

Efficient 1,3-Oxazolidin-2-one Synthesis through Heterogeneous PdII-Catalyzed Intramolecular Hydroamination of Propargylic Carbamates

Journal

CHEMISTRY-A EUROPEAN JOURNAL
Volume 25, Issue 25, Pages 6295-6299

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201900678

Keywords

cycloisomerization; heterogeneous catalysis; mesoporous silica; oxazolidinones; palladium

Funding

  1. European Research Council [ERC AdG 247014]
  2. Swedish Research Council [2016-03897]
  3. Berzelii Center EXSELENT
  4. Knut and Alice Wallenberg Foundation [KAW 2016.0072]

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Herein, we present an operationally simple protocol for the cycloisomerization of propargylic carbamates in which a heterogeneous catalyst consisting of Pd species immobilized on amino-functionalized siliceous mesocellular foam (Pd-II-AmP-MCF) is used. This Pd nanocatalyst displayed high efficiency at low catalyst loading and reaction temperatures, which allowed for the efficient and mild synthesis of a wide range of 1,3-oxazolidin-2-one derivatives and related compounds. Moreover, it proved possible to re-use the Pd nanocatalyst for several reactions, although a gradual decrease in activity was observed in the subsequent cycles.

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