Palladium supported on an amphiphilic porous organic polymer: a highly efficient catalyst for aminocarbonylation reactions in water

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The development of environmentally friendly heterogeneous catalysts for organic reactions in water is becoming of growing importance for the development of sustainable processes. In this work, a porous organic polymer‐supported palladium catalyst (Pd@UPOP‐1) was successfully fabricated from 3,3′‐diaminobenzidine and methylenediphenyl diisocyanate through a facile urea‐forming condensation reaction. The structure and composition of the catalyst were characterized using several physicochemical methods. Pd@UPOP‐1 was found to possess good porous structure and excellent amphiphilicity. Under mild reaction conditions, the catalyst showed excellent catalytic activity and good substrate compatibility for the Suzuki–Miyaura coupling reaction of aryl bromides, as well as the hydroxycarbonylation reaction of aryl iodides. In addition, the catalyst could be used for several consecutive recycles in both cases.

Section: Resultsmentioning

confidence: 75%

Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

Urea‐based amphiphilic porous organic polymer‐supported palladium as a reusable catalyst for Suzuki–Miyaura coupling and hydroxycarbonylation reactions in water

Lei

Lan

Zhu

et al. 2018

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Pd/C: An efficient and reusable catalyst for the synthesis of flavones via carbonylation of aryl halides

Lei

Zhi

Wan

et al. 2017

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This work describes an efficient and mild approach for the synthesis of flavones via catalytic carbonylation of aryl halides with 2‐hydroxyacetophenone using the commercial Pd/C as an efficient, heterogeneous and recyclable catalyst. Under balloon pressure of CO, 0.6 mol% Pd/C is sufficient for moderate yields of flavones for the carbonylation of aryl iodides under phosphine‐free conditions and aryl bromides in the presence of phosphine ligand. The catalyst is easily separable and shows significant recyclability. Moreover, the reaction mechanism was discussed, and a possible mechanism that contains two different cyclisation pathways was proposed.

Carbonylative Suzuki coupling and alkoxycarbonylation of aryl halides using palladium supported on phosphorus‐doped porous organic polymer as an active and robust catalyst

Wan

Song

et al. 2018

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Developing highly active catalysts with the combined advantages of molecular and solid catalysis is considered as the “Holy Grail” in the area of catalysis research. Herein, a phosphorus‐doped porous polymer‐immobilized palladium was successfully developed as an efficient, robust, and recyclable catalyst for the carbonylative Suzuki coupling and alkoxycarbonylation reactions of aryl halides. Rather than just as an immobilizing molecular catalyst, palladium supported on phosphorus‐doped porous organic polymer exhibits even better catalytic performances than that of its analogue homogeneous catalysts in both carbonylation reactions. Moreover, the catalyst can be easily separated and reused for at least 5 times without significant loss in reactivity. Importantly, the catalyst was highly stable under carbonylation reaction conditions, and no palladium nanoparticle was observed even after the 5th reuse.