| Autor: |
Schlimpen F; Laboratoire de Synthèse, Réactivité Organique et Catalyse (LASYROC), Institut de Chimie, CNRS-UMR7177, Université de Strasbourg, 4 rue Blaise Pascal, Strasbourg 67070, France., Plaçais C; Laboratoire de Synthèse, Réactivité Organique et Catalyse (LASYROC), Institut de Chimie, CNRS-UMR7177, Université de Strasbourg, 4 rue Blaise Pascal, Strasbourg 67070, France., Starck E; Laboratoire de Synthèse, Réactivité Organique et Catalyse (LASYROC), Institut de Chimie, CNRS-UMR7177, Université de Strasbourg, 4 rue Blaise Pascal, Strasbourg 67070, France., Bénéteau V; Laboratoire de Synthèse, Réactivité Organique et Catalyse (LASYROC), Institut de Chimie, CNRS-UMR7177, Université de Strasbourg, 4 rue Blaise Pascal, Strasbourg 67070, France., Pale P; Laboratoire de Synthèse, Réactivité Organique et Catalyse (LASYROC), Institut de Chimie, CNRS-UMR7177, Université de Strasbourg, 4 rue Blaise Pascal, Strasbourg 67070, France., Chassaing S; Laboratoire de Synthèse, Réactivité Organique et Catalyse (LASYROC), Institut de Chimie, CNRS-UMR7177, Université de Strasbourg, 4 rue Blaise Pascal, Strasbourg 67070, France. |
| Abstrakt: |
The potential of copper(I)-zeolite catalysis was evaluated in the three-component KA 2 -coupling mediated synthesis of α-tertiary propargylamines. Our archetypal copper(I)-doped zeolite Cu I -USY proved to be efficient under ligand- and solvent-free conditions at 80 °C. Usable up to four times, this catalytic material enables the coupling of diverse ketones, alkynes, and amines with a broad functional group tolerance. A decarboxylative and a desilylative version, respectively, involving an alkynoic acid and trimethylsilylacetylene as alkyne surrogates, was also set up to bypass selectivity issues and/or to access α-tertiary propargylamines that are unattainable under standard KA 2 conditions. Interestingly, the KA 2 -type coupling reactions were successfully linked to other Cu I -catalyzed reactions, thus resulting in sequential one-pot processes under full Cu I -USY catalysis. |
