Rosa Pich, Sonia Ladeira, Pierre Lavedan, Jean-François Lahitte, Jean-Christophe Remigy, Daniel Pla, Montserrat Gómez

A mechanistic insight on CuI‐catalyzed synthesis of oxazolidinones through a four‐component reaction

  • General Chemistry

In this contribution, we describe a straightforward and efficient synthesis of oxazolidin‐2‐ones through a Cu(I)‐catalyzed four‐component coupling of amines, aldehydes, terminal alkynes, and CO2 via carboxylative cyclization of propargyl amine intermediates. This strategy enables the selective synthesis of a variety of (Z)‐5‐alkylidene‐oxazolidin‐2‐ones substituted in position 3 and 4 of the heterocyclic core with a variety of functional groups, well‐tolerated in terms of scope. A mechanistic study was carried out monitoring the process by different techniques (operando FTIR, multi‐nuclear NMR), with the aim of identifying the intermediates, both organic compounds and Cu(I) coordination complexes, which showed the plausible multi‐metallic nature of the catalytic intermediates (identified by X‐ray diffraction analyses on monocrystal).

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