Affiliation:
1. Laboratoire Hétérochimie Fondamentale et Appliquée UMR CNRS 5069 Université Toulouse 3 – Paul Sabatier 118 route de Narbonne 31062 Toulouse Cedex 09 France
2. Université de Toulouse INPT, UPS, UMR CNRS 5503 Laboratoire de Génie Chimique 118 Route de Narbonne 31062 Toulouse Cedex 09 France
3. Institut de Chimie de Toulouse UAR 2599 118 Route de Narbonne 31062 Toulouse Cedex 09 France
Abstract
AbstractIn 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 propargylamine intermediates. This strategy enables the selective synthesis of a variety of (Z)‐5‐alkylidene‐oxazolidin‐2‐ones substituted in positions 3, 4 and 5 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 in solution 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).