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Efficient 1,3-Oxazolidin-2-one Synthesis through Heterogeneous PdII-Catalyzed Intramolecular Hydroamination of Propargylic Carbamates
Authors:Michael Oschmann  Clotilde Placais  Anuja Nagendiran  Prof. Jan-E. Bäckvall  Dr. Oscar Verho
Affiliation:Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, 10691 Stockholm, Sweden
Abstract: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 (PdII-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.
Keywords:cycloisomerization  heterogeneous catalysis  mesoporous silica  oxazolidinones  palladium
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