期刊
NANOMATERIALS
卷 11, 期 10, 页码 -出版社
MDPI
DOI: 10.3390/nano11102702
关键词
carbon nanotubes; copper complexes; P-ligands; PTA; click chemistry; Azide-Alkyne cycloaddition; supported catalysis
类别
资金
- Fundacao para a Ciencia e a Tecnologia (FCT), Portugal of the Centro de Quimica Estrutural, FCT/MCTES from Associate Laboratory for Green Chemistry-LAQV, Scientific Employment Stimulus-Institutional Call [UIDB/00100/2020, UIDB/50006/2020, UIDP/50006/2020, CEECINST/00102/2018]
- RUDN University Strategic Academic Leadership Program
- FCT through the CATSUS PhD Program [PD/BD 135555/2018]
- Instituto Superior Tecnico, Portugal [CO2usE-1801P.00867.1.01, IST-ID/263/2019]
Three hydrophilic PTA ammonium salts were synthesized through N-alkylation and used to prepare a new set of water-soluble copper(I) complexes, which showed high catalytic activity in one-pot azide-alkyne cycloaddition reactions. The most active catalysts were immobilized on activated carbon and carbon nanotubes, displaying efficient catalytic performance and recyclability.
The N-alkylation of 1,3,5-triaza-7-phosphaadamantane (PTA) with ortho-, meta- and para-substituted nitrobenzyl bromide under mild conditions afforded three hydrophilic PTA ammonium salts, which were used to obtain a new set of seven water-soluble copper(I) complexes. The new compounds were fully characterized and their catalytic activity was investigated for the low power microwave assisted one-pot azide-alkyne cycloaddition reaction in homogeneous aqueous medium to obtain disubstituted 1,2,3-triazoles. The most active catalysts were immobilized on activated carbon (AC), multi-walled carbon nanotubes (CNT), as well as surface functionalized AC and CNT, with the most efficient support being the CNT treated with nitric acid and NaOH. In the presence of the immobilized catalyst, several 1,4-disubstituted-1,2,3-triazoles were obtained from the reaction of terminal alkynes, organic halides and sodium azide in moderate yields up to 80%. Furthermore, the catalyzed reaction of terminal alkynes, formaldehyde and sodium azide afforded 2-hydroxymethyl-2H-1,2,3-triazoles in high yields up to 99%. The immobilized catalyst can be recovered and recycled through simple workup steps and reused up to five consecutive cycles without a marked loss in activity. The described catalytic systems proceed with a broad substrate scope, under microwave irradiation in aqueous medium and according to click rules .
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