Sub-2nm palladium nanoparticles were successfully constructed by anchoring Pd(OAc)2 into an amine-functionalized and highly porous metal organic framework (UIO-66-NH2) and successive reduction by H2 (Pd0@UIO-66-NH2).The catalyst Pd0@UIO-66-NH2 exhibited excellent performance (up to 99% yield for biphenyl compounds) in the Suzuki coupling reaction of halogenated benzene with phenylboronic acid.Moreover,the catalyst behaved well substrate compatibility.In addition,the catalyst can be recycled by simple filtration and performed stable reusability for at least 5 times.It was found that the efficient catalytic performance and high stability of Pd0@UIO-66-NH2 were mainly attributed to the cavity confinement effect,high porous and the free amino groups of the supporter UIO-66-NH2.
[1] Yi H,Zhang G T,Wang H M,et al.Recent advances in radical C—H activation/radical cross-coupling[J].Chemical Reviews,2017,117(13):9016-9085.
[2] Dhakshinamoorthy A,Asiri A M,Garcia H.Metal-organic frameworks catalyzed C—C and C-heteroatom coupling reactions[J].Chemical Society Reviews,2015,44(7):1922-1947.
[3] He J,Wasa M,Chan K S L,et al.Palladium-catalyzed transformations of alkyl C—H bonds[J].Chemical Reviews,2016,117(13):8754-8786.
[4] Li Z,Liu L.Recent advances in mechanistic studies on Ni catalyzed cross-coupling reactions[J].Chinese Journal of Catalysis,2015,36(1):3-14.
[5] DelZotto A,Zuccaccia D.Metallic palladium,PdO,and palladium supported on metal oxides for the Suzuki-Miyaura cross-coupling reaction:a unified view of the process of formation of the catalytically active species in solution[J].Catalysis Science & Technology,2017,7(18):3934-3951.
[6] Yang Q H,Xu Q,Jiang H L.Metal-organic frameworks meet metal nanoparticles:synergistic effect for enhanced catalysis[J].Chemical Society Reviews,2017,46(15):4774-4808.
[7] 张伊,顾奕奕,陈云琳,等.掺杂金属离子对MOF-5吸附甲烷分子的影响[J].化工新型材料,2015,43(2):93-96.
[8] Yu J,Mu C,Yan B,et al.Nanoparticle/MOF composites:preparations and applications[J].Materials Horizons,2017,4(4):557-569.
[9] Li X Y,Li Y Z,Yang Y,et al.Efficient light hydrocarbon separation and CO2 capture and conversion in a stable MOF with oxalamide-decorated polar tubes[J].Chemical Communications,2017,53(96):12970-12973.
[10] Zheng H Q,Zhang Y N,Liu L F,et al.One-pot synthesis of metal-organic frameworks with encapsulated target molecules and their applications for controlled drug delivery[J].Journal of the American Chemical Society,2016,138(3):962-968.
[11] Zhao S N,Song X Z,Song S Y,et al.Highly efficient heterogeneous catalytic materials derived from metal-organic framework supports/precursors[J].Coordination Chemistry Reviews,2017,337:80-96.
[12] Wu C D,Zhao M.Incorporation of molecular catalysts in metal-organic frameworks for highly efficient heterogeneous catalysis[J].Advanced Materials,2017,29(14):1605446.
[13] 牛照栋,周玲玲,关清卿,等.双金属类MOF材料的制备及应用[J].化工新型材料,2019,47(8):5-8.
[14] 樊荣,薛建军,赵媛,等.MOF(Co)/功能化石墨烯制备高效Co-N-C型氧还原催化剂研究[J].化工新型材料,2019,47(3):165-171.
[15] Dhakshinamoorthy A,Asiri A M,Garcia H.Metal organic frameworks as versatile hosts of Au nanoparticles in heterogeneous catalysis[J].ACS Catalysis,2017,7(4):2896-2919.
[16] Han Y Q,Xu H T,Su Y Q,et al.Noble metal (Pt,Au@Pd) nanoparticles supported on metal organic framework (MOF-74) nanoshuttles as high-selectivity CO2 conversion catalysts[J].Journal of Catalysis,2019,370:70-78.
[17] Wang D K,Pan Y T,Xu L Z,et al.PdAu@MIL-100(Fe) cooperatively catalyze tandem reactions between amines and alcohols for efficient N-alkyl amines syntheses under visible light[J].Journal of Catalysis,2018,361:248-254.
[18] Xu B,Li X J,Chen Z M,et al.Pd@MIL-100(Fe) composite nanoparticles as efficient catalyst for reduction of 2/3/4-nitrophenol:synergistic effect between Pd and MIL-100(Fe)[J].Microporous and Mesoporous Materials,2018,255:1-6.
[19] Ding Z Q,Wang K,Mai Z Q,et al.RhRu alloyed nanoparticles confined within metal organic frameworks for electrochemical hydrogen evolution at all pH values[J].International Journal of Hydrogen Energy,2019,44(45):24680-24689.
[20] Pourkhosravani M,Dehghanpour S,Farzaneh F.Palladium nanoparticles supported on zirconium metal organic framework as an efficient heterogeneous catalyst for the Suzuki-Miyaura coupling reaction[J].Catalysis Letters,2016,146(2):499-508.
[21] Zhang Y Y,Li J X,Ding L L,et al.Palladium nanoparticles encapsulated in the MIL-101-catalyzed one-pot reaction of alcohol oxidation and aldimine condensation[J].Inorganic Chemistry,2018,57(21):13586-13593.
[22] Choi S,Oh M.Well-arranged and confined incorporation of PdCo nanoparticles within a hollow and porous metal-organic framework for superior catalytic activity[J].AngewandteChemie International Edition,2019,58(3):866-871.
[23] Martis M,Mori K,Fujiwara K,et al.Amine-functionalized MIL-125 with imbedded palladium nanoparticles as an efficient catalyst for dehydrogenation of formic acid at ambient temperature[J].The Journal of Physical Chemistry C,2013,117(44):22805-22810.
[24] Zhang F M,Zheng S,Xiao Q,et al.Synergetic catalysis of palladium nanoparticles encaged within amine-functionalized UiO-66 in the hydrodeoxygenation of vanillin in water[J].Green Chemistry,2016,18(9):2900-2908.
[25] Xu X Y,Yan B.Eu(Ⅲ) functionalized Zr-based metal-organic framework as excellent fluorescent probe for Cd2+ detection in aqueous environment[J].Sensors and Actuators B:Chemical,2016,222:347-353.
[26] Augustyniak A W,Sadakiyo M,Navarro J A R,et al.Design of shape-palladium nanoparticles anchored on titanium(Ⅳ) metal-organic framework:highly active catalysts for reduction of p-nitrophenol in water[J].ChemistrySelect,2018,3(27):7934-7939.
[27] Liu Y Q,Zhou Y,Li J,et al.Direct aerobic oxidative homocoupling of benzene to biphenyl over functional porous organic polymer supported atomically dispersed palladium catalyst[J].Applied Catalysis B:Environmental,2017,209:679-688.
[28] Guan Q Q,Wang B,Chai X S,et al.Comparison of Pd-UiO-66 and Pd-UiO-66-NH2 catalysts performance for phenol hydrogenation in aqueous medium[J].Fuel,2017,205:130-141.
[29] Neeli C K P,Puthiaraj P,Lee Y R,et al.Transfer hydrogenation of nitrobenzene to aniline in water using Pd nanoparticles immobilized on amine-functionalized UiO-66[J].Catalysis Today,2018,303:227-234.
[30] Liu X,Ning P,Xu L S,et al.Low-temperature catalytic oxidation of CO over highly active mesoporous Pd/CeO2-ZrO2-Al2O3 catalyst[J].RSC Advances,2016,6(47):41181-41188.
基金资助
国家自然科学基金项目(21802119);国家自然科学基金项目(21906140)
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