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Efficient 1,3‐Oxazolidin‐2‐one Synthesis through Heterogeneous Pd II ‐Catalyzed Intramolecular Hydroamination of Propargylic Carbamates
Author(s) -
Oschmann Michael,
Placais Clotilde,
Nagendiran Anuja,
Bäckvall JanE.,
Verho Oscar
Publication year - 2019
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201900678
Subject(s) - hydroamination , cycloisomerization , catalysis , intramolecular force , chemistry , combinatorial chemistry , reaction conditions , palladium , organic chemistry
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.