Covalent triazine framework-supported palladium nanoparticles for catalytic hydrogenation of N-heterocycles

Abstract

A covalent triazine framework (CTF) with high surface area, high amount nitrogen functionalities, porosity and basicity was employed as support for palladium nanoparticles (NPs). Well dispersed Pd/CTF-1 catalyst with uniform distribution of Pd particles was successfully synthesized in the present study. The as-prepared 4% Pd/CTF-1 catalyst showed a markedly improved activity in hydrogenation of N-heterocyclic compounds as compared to the activated carbon (AC) supported catalyst, i.e., Pd/CTF-1 10 catalyst exhibits ca. 3.6 times faster than that of Pd/AC on the hydrogenation of N-methylpyrrole. Characterizations on Pd/CTF indicated the electron donation from N in CTF to metallic Pd NPs, showing the intensified electronic interaction between the Pd NPs and CTF support, which is responsible for the enhanced activities on the catalytic hydrogenation of N-heterocycles.

Covalent Triazine‐based Frameworks—Tailor‐made Catalysts and Catalyst Supports for Molecular and Nanoparticulate Species

“…The good dispersion and narrow particles ize distribution was also reported to enhancet he hydrogenation of N-heterocyclic compounds for Pd/CTFc atalysts. [109] Once again, improveda ctivities were attributedt ot he electron donating properties of the N-moieties within the support. Activity only decreased slightly over recycling experiments.T he same system can be applied in the ligand and additive-frees elective double carbonylation of aryl iodidesu nder ambient CO pressure.…”

“…The good dispersion and narrow particle size distribution was also reported to enhance the hydrogenation of N ‐heterocyclic compounds for Pd/CTF catalysts . Once again, improved activities were attributed to the electron donating properties of the N ‐moieties within the support.…”

Covalent Organic Frameworks and Cage Compounds: Design and Applications of Polymeric and Discrete Organic Scaffolds

“…[331] In comparison to the molecular cobalt complex, the activity was enhanced by afactor of 26 and no degradation was observed over 24 h. Coating of CTF-1 with Pd nanoparticles resulted in acatalyst that exhibited a3.6 times faster reduction of N-methylpyrrole compared to an activated carbon-supported catalyst. [332] COFs have also been used as aheterogeneous matrix for chiral organocatalysts.P ostsynthetic modification of COFs with chiral pyrrolidines established aheterogeneous platform for asymmetric Michael additions with ee values up to 92 %. [185] Thed irect implementation of chiral side chains [186] or intrinsically chiral building blocks [181,187] also resulted in highly active catalysts for various organic reactions.Banerjee and co-workers combined both acidic and basic sites in one bifunctional COF material (Figure 19), which was used to catalyze the tandem reaction of acetal-protected benzaldehyde with malononitrile.…”

Kovalente organische Netzwerke und Käfigverbindungen: Design und Anwendungen von polymeren und diskreten organischen Gerüsten

“…Die Beschichtung von CTF-1 mit Pd-Nanopartikeln ergab einen Katalysator,d er N-Methylpyrrol 3.6-mal schneller reduziert als ein vergleichbarer Pd-C-Katalysator. [332] COFs wurden auch als Heterogenmatrices fürc hirale Organokatalysatoren eingesetzt. Die postsynthetische Modifikation von COFs mit chiralen Pyrrolidinen lieferte eine heterogene Plattform fürasymmetrische Michael-Additionen mit ee-Werten bis zu 92 %.…”