Chemical Science Symposium 2022

Copper(II) trilfate-catalyzed three-component reaction for the conversion of allyl alcohol into 1-aryl-2-amino-propanes Camilla Loro, Gianluigi Broggini Università degli Studi dell'Insubria, Italy Hydroamination procedures on non-activated alkenes have received significant attentions to access fine chemicals or building blocks in organic synthesis. Among the various transition-metal catalysts usually employed to achieve C-N bond formation, copper(II) salts and complexes were proven to be highly performing. 1 In the field of hydroamination and carboamination procedure, copper(II) triflate was widely used either as catalyst or as Lewis acid. Moreover, recent studies have shown that metal triflates can be used also for the in situ generation of triflic acid which could be exploited in reactions involving carbocation intermediates. 2 Following our interest toward cascade procedures, 3 we developed a copper(II) triflate-promoted arylation/ hydroamination of O -allyl N -sulphonyl carbamates in the presence of arenes providing 1-aryl-2-aminopropanes. 4 Recently, we investigated a more efficient method to synthesize the same kind of products through a three- component procedure. This copper-catalyzed process involves easy accessible allyl alcohols as C3 synthons, sulfonamides, and aromatic partners in the presence of a phosphine ligand which makes milder the reaction conditions. The detailed mechanism for this C-H based cascade reaction will be discussed in the poster. References 1. Q.-F. Xu-Xu, Q.-Q. Liu, X. Zhang, S.-L. You, Angew. Chem. Int. Ed., 2018 , 57 , 15204 2. M. J.-L. Tschan, C. M. Thomas, H. Strub, J.-F. Carpentier, Adv. Synth. Catal. , 2009 , 351 , 2496 3. F. Foschi, C. Loro, R. Sala, J. Oble, L. Lo Presti, E. M. Beccalli, G. Poli, G. Broggini, Org. Lett., 2020 , 22 , 1402 4. C. Loro, J. Oble, F. Fosch, M. Papis, E. M. Beccalli, S. Giofrè, G. Poli, G. Broggini, Org. Chem. Front ., 2022 , 9 , 1711

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