Our research group has previously reported the preparation of gold nanoparticles (AuNPs) supported on different functionalized silica supports. We started using commercial polyethyleneimine-functionalized silica bead [1] and we continued preparing silica nanoparticles functionalized with alkynyl carbamate moieties. [2] Recently, we have focused on the straightforward synthesis of AuNPs anchored on commercial, micrometric oxide supports (i.e. SiO2, Al2O3, TiO2) previously modified with the di-functional organosilane [3-(2-propynylcarbamate)propyl]triethoxysilane (PPTEOS) by a grafting procedure. After being thoroughly characterized by several complementary techniques (XPS, TEM, SSNMR, AAS etc.), the catalytic activity of these systems (Au/OS@Yne) has been evaluated in the oxidation of alcohols both in batch and continuous-flow systems. [3] Furthermore, we have extended the same synthetic procedure to the preparation of a novel and magnetically recoverable catalyst, consisting of AuNPs supported on functionalized nano-magnetite (Au/Fe3O4@Yne). We now present the latest results obtained in the study of the catalytic application of Au/SiO2@Yne and Au/Fe3O4@Yne in the alkynes hydroamination reaction, which is considered the most atom efficient process for the formation of a series of nitrogen-containing compounds. Indeed, this transformation takes place without the formation of any side product and leads to the production of enamine, imine or substituted amines, which have a significant importance as bulk and fine chemicals or building blocks in organic synthesis. [1] S. Fazzini , D. Nanni , B. Ballarin , M. C. Cassani , M. Giorgetti , C. Maccato, A. Trapananti, G. Aquilanti and S. I. Ahmed, J. Phys. Chem. C. 2012, 116, 25434−25443; M. Giorgetti, G. Aquilanti, B. Ballarin, M. Berrettoni, M. C. Cassani, S. Fazzini, D. Nanni and D. Tonelli, Anal. Chem. 2016, 88, 6873-6880; [2] S. Fazzini, M. C. Cassani, B. Ballarin, E. Boanini, J. S. Girardon, A.S. Mamede, A. Mignani and D. Nanni, J. Phys. Chem. C. 2014, 118, 24538-24547; M. C. Cassani, B. Ballarin, D. Barreca, E. Boanini, E. Bonansegna, G. Carraro, S. Fazzini, A. Mignani, D. Nanni, D. Pinelli, RSC Adv. 2016, 6, 25780-25788. [3] B. Ballarin, D. Barreca, E. Boanini, M. C. Cassani, P. Dambruoso, A. Massi, A. Mignani, D. Nanni, C. Parise, A. Zaghi, ACS Sus. Chem. Eng. 2017, 5, 4746-4756.
Chiara, P., Maria Cristina Cassani, ., Barbara, B., Daniele, N. (2017). Supported gold nanoparticles catalysts for alkynes hydroamination.
Supported gold nanoparticles catalysts for alkynes hydroamination
Chiara Parise
;Maria Cristina Cassani;Barbara Ballarin;Daniele Nanni
2017
Abstract
Our research group has previously reported the preparation of gold nanoparticles (AuNPs) supported on different functionalized silica supports. We started using commercial polyethyleneimine-functionalized silica bead [1] and we continued preparing silica nanoparticles functionalized with alkynyl carbamate moieties. [2] Recently, we have focused on the straightforward synthesis of AuNPs anchored on commercial, micrometric oxide supports (i.e. SiO2, Al2O3, TiO2) previously modified with the di-functional organosilane [3-(2-propynylcarbamate)propyl]triethoxysilane (PPTEOS) by a grafting procedure. After being thoroughly characterized by several complementary techniques (XPS, TEM, SSNMR, AAS etc.), the catalytic activity of these systems (Au/OS@Yne) has been evaluated in the oxidation of alcohols both in batch and continuous-flow systems. [3] Furthermore, we have extended the same synthetic procedure to the preparation of a novel and magnetically recoverable catalyst, consisting of AuNPs supported on functionalized nano-magnetite (Au/Fe3O4@Yne). We now present the latest results obtained in the study of the catalytic application of Au/SiO2@Yne and Au/Fe3O4@Yne in the alkynes hydroamination reaction, which is considered the most atom efficient process for the formation of a series of nitrogen-containing compounds. Indeed, this transformation takes place without the formation of any side product and leads to the production of enamine, imine or substituted amines, which have a significant importance as bulk and fine chemicals or building blocks in organic synthesis. [1] S. Fazzini , D. Nanni , B. Ballarin , M. C. Cassani , M. Giorgetti , C. Maccato, A. Trapananti, G. Aquilanti and S. I. Ahmed, J. Phys. Chem. C. 2012, 116, 25434−25443; M. Giorgetti, G. Aquilanti, B. Ballarin, M. Berrettoni, M. C. Cassani, S. Fazzini, D. Nanni and D. Tonelli, Anal. Chem. 2016, 88, 6873-6880; [2] S. Fazzini, M. C. Cassani, B. Ballarin, E. Boanini, J. S. Girardon, A.S. Mamede, A. Mignani and D. Nanni, J. Phys. Chem. C. 2014, 118, 24538-24547; M. C. Cassani, B. Ballarin, D. Barreca, E. Boanini, E. Bonansegna, G. Carraro, S. Fazzini, A. Mignani, D. Nanni, D. Pinelli, RSC Adv. 2016, 6, 25780-25788. [3] B. Ballarin, D. Barreca, E. Boanini, M. C. Cassani, P. Dambruoso, A. Massi, A. Mignani, D. Nanni, C. Parise, A. Zaghi, ACS Sus. Chem. Eng. 2017, 5, 4746-4756.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
