Terminal alkynes hydroamination catalized by copper nanoparticles

JUAN MANCEBO ARACIL; BELÉN ALONSO; GABRIEL RADIVOY

Santiago de Compostela

Conferencia; ECSOC.- The 24th International Electronic Conference on Synthetic Organic Chemistry; 2020

Universidad de Santiago de Compostela

Nitrogen-containingcompounds, such as amines, enamines and imines, are valuable and of greatindustrial and pharmaceutical relevance. The hydroamination (HA) is a reactionthat involve the direct formation of a new C-N bond by addition of an amine to anunsaturated CC bond. HA is one of the most atom efficient processes and can beperformed under catalysis of a wide range of metals, being especially versatilethe late-transition metals.In this work wepresent a study of the reaction of hydroamination of terminal alkynes catalyzedby supported-copper nanoparticles, with very low catalyst loading (< 2 mol%).Through themethodology of our research group, which involve the addition of the support toa suspension of freshly prepared copper nanoparticles, a wide range of terminalalkynes were regioselectively converted to imines by intermolecular HA. Imineswere obtained in moderate to quantitative yields, which were then easilyreduced to the corresponding amines.Finally, the heterogeneous and low-cost coppercatalyst can be reused in several catalytic cycles with no yield andselectivity decrease.