Key Laboratory of Biomass Chemical Engineering of Ministry of Education, College of Chemical and Biological Engineering, Zhejiang University, Hangzhou 310027, China
We have successfully prepared a series of Pd-Ni/TiO2 catalysts by a one-step impregnation-reduction method. Among these catalysts with different compositions of Ni and Pd, the one with the Ni:Pd ratio of 2.95 showed the best activity. Small monodispersed Pd-Ni bimetallic nanoparticles were loaded on the surface of titanium oxide nanopowder as confirmed with TEM and EDS mapping. The XPS analysis demonstrated that Pd exists as 31% Pd(II) species and 69% Pd(0) species and all nickel is Ni(II). The prepared Pd-Ni/TiO2 exhibited enhanced catalytic activity compared to an equal amount of Pd/TiO2 for Suzuki-Miyaura reactions together with excellent applicability and reusability.
Crane E A, Scheidt K A. Prins-type macrocyclizations as an efficient ring-closing strategy in natural product synthesis. Angewandte Chemie International Edition, 2010, 49(45): 8316–8326 https://doi.org/10.1002/anie.201002809
2
Dumas A, Spicer C D, Gao Z, Takehana T, Lin Y A, Yasukohchi T, Davis B G. Self-liganded Suzuki-Miyaura coupling for site-selective protein PEGylation. Angewandte Chemie International Edition, 2013, 52(14): 3916–3921 https://doi.org/10.1002/anie.201208626
3
Maluenda I, Navarro O. Recent developments in the Suzuki-Miyaura reaction: 2010‒2014. Molecules (Basel, Switzerland), 2015, 20(5): 7528–7557 https://doi.org/10.3390/molecules20057528
4
Miyaura N, Suzuki A. Stereoselective synthesis of arylated (E)-alkenes by the reaction of alk-1-enylboranes with aryl halides in the presence of palladium catalyst. Chemical Communications, 1979, 19(19): 866–867 https://doi.org/10.1039/c39790000866
5
Rossi R, Bellina F, Lessi M, Manzini C, Marianetti G A, Perego L. Recent applications of phosphane-based palladium catalysts in Suzuki-Miyaura reactions involved in total syntheses of natural products. Current Organic Chemistry, 2015, 19(14): 1302–1409 https://doi.org/10.2174/1385272819666150506230050
6
Yamaguchi J, Yamaguchi A D, Itami K. C‒H bond functionalization: Emerging synthetic tools for natural products and pharmaceuticals. Angewandte Chemie International Edition, 2012, 51(36): 8960–9009 doi:10.1002/anie.201201666
7
Yokoyama A, Suzuki H, Kubota Y, Ohuchi K, Higashimura H, Yokozawa T. Chain-growth polymerization for the synthesis of polyfluorene via Suzuki-Miyaura coupling reaction from an externally added initiator unit. Journal of the American Chemical Society, 2007, 129(23): 7236–7237 https://doi.org/10.1021/ja070313v
8
Pagliaro M, Pandarus V, Ciriminna R, Béland F, Demma Carà P. Heterogeneous versus homogeneous palladium catalysts for cross-coupling reactions. ChemCatChem, 2012, 4(4): 432–445 https://doi.org/10.1002/cctc.201100422
9
Que Y, Feng C, Zhang S, Huang X. Stability and catalytic activity of PEG-b-PS-capped gold nanoparticles: A matter of PS chain length. Journal of Physical Chemistry C, 2015, 119(4): 1960–1970 https://doi.org/10.1021/jp511850v
10
Chen J, Zhang Z, Bao Z, Su Y, Xing H, Yang Q, Ren Q. Functionalized metal-organic framework as a biomimetic heterogeneous catalyst for transfer hydrogenation of imines. ACS Applied Materials & Interfaces, 2017, 9(11): 9772–9777 https://doi.org/10.1021/acsami.7b00562
11
Chtchigrovsky M, Lin Y, Ouchaou K, Chaumontet M, Robitzer M, Quignard F, Taran F. Dramatic effect of the gelling cation on the catalytic performances of alginate-supported palladium nanoparticles for the Suzuki-Miyaura reaction. Chemistry of Materials, 2012, 24(8): 1505–1510 https://doi.org/10.1021/cm3003595
12
Jiang B, Song S, Wang J, Xie Y, Chu W, Li H, Xu H, Tian C, Fu H. Nitrogen-doped graphene supported Pd@PdO core-shell clusters for C‒C coupling reactions. Nano Research, 2014, 7(9): 1280–1290 https://doi.org/10.1007/s12274-014-0492-1
13
Sun J, Fu Y, He G, Sun X, Wang X. Green Suzuki-Miyaura coupling reaction catalyzed by palladium nanoparticles supported on graphitic carbon nitride. Applied Catalysis B: Environmental, 2015, 165: 661–667 https://doi.org/10.1016/j.apcatb.2014.10.072
14
Zhang L, Feng C, Gao S, Wang Z, Wang C. Palladium nanoparticle supported on metal-organic framework derived N-decorated nanoporous carbon as an efficient catalyst for the Suzuki coupling reaction. Catalysis Communications, 2015, 61: 21–25 https://doi.org/10.1016/j.catcom.2014.12.004
15
Ohtaka A, Sansano J M, Nájera C, Miguel-García I, Berenguer-Murcia Á, Cazorla-Amorós D. Palladium and bimetallic palladium-nickel nanoparticles supported on multiwalled carbon nanotubes: Application to carbon-carbon bond-forming reactions in water. ChemCatChem, 2015, 7(12): 1841–1847 https://doi.org/10.1002/cctc.201500164
16
Song H, Zhu Q, Zheng X, Chen X. One-step synthesis of three-dimensional graphene/multiwalled carbon nanotubes/Pd composite hydrogels: An efficient recyclable catalyst for Suzuki coupling reactions. Journal of Materials Chemistry. A, Materials for Energy and Sustainability, 2015, 3(19): 10368–10377 https://doi.org/10.1039/C5TA00280J
17
Hu J, Yang Q, Yang L, Zhang Z, Su B, Bao Z, Ren Q, Xing H, Dai S. Confining noble metal (Pd, Au, Pt) nanoparticles in surfactant ionic liquids: Active non-mercury catalysts for hydrochlorination of acetylene. ACS Catalysis, 2015, 5(11): 6724–6731 https://doi.org/10.1021/acscatal.5b01690
18
Wu Y, Wang D, Zhao P, Niu Z, Peng Q, Li Y. Monodispersed Pd-Ni nanoparticles: Composition control synthesis and catalytic properties in the Miyaura-Suzuki reaction. Inorganic Chemistry, 2011, 50(6): 2046–2048 https://doi.org/10.1021/ic102263b
19
Cai S, Wang D, Niu Z, Li Y. Progress in organic reactions catalyzed by bimetallic nanomaterials. Chinese Journal of Catalysis, 2013, 34(11): 1964–1974 https://doi.org/10.1016/S1872-2067(12)60701-3
20
Gu J, Zhang Y W, Tao F. Shape control of bimetallic nanocatalysts through well-designed colloidal chemistry approaches. Chemical Society Reviews, 2012, 41(24): 8050–8065 https://doi.org/10.1039/c2cs35184f
21
Chen T, Rodionov V O. Controllable catalysis with nanoparticles: Bimetallic alloy systems and surface adsorbates. ACS Catalysis, 2016, 6(6): 4025–4033 https://doi.org/10.1021/acscatal.6b00714
22
Shaabani A, Mahyari M. PdCo bimetallic nanoparticles supported on PPI-grafted graphene as an efficient catalyst for Sonogashira reactions. Journal of Materials Chemistry. A, Materials for Energy and Sustainability, 2013, 1(32): 9303–9311 https://doi.org/10.1039/c3ta11706e
23
Nath Dhital R, Kamonsatikul C, Somsook E, Sakurai H. Bimetallic gold-palladium alloy nanoclusters: An effective catalyst for Ullmann coupling of chloropyridines under ambient conditions. Catalysis Science & Technology, 2013, 3(11): 3030–3035 https://doi.org/10.1039/c3cy00303e
24
Tan L, Wu X, Chen D, Liu H, Meng X, Tang F. Confining alloy or core-shell Au-Pd bimetallic nanocrystals in silica nanorattles for enhanced catalytic performance. Journal of Materials Chemistry. A, Materials for Energy and Sustainability, 2013, 1(35): 10382–10388 https://doi.org/10.1039/c3ta11749a
25
Alonso A, Shafir A, Macanás J, Vallribera A, Muñoz M, Muraviev D N. Recyclable polymer-stabilized nanocatalysts with enhanced accessibility for reactants. Catalysis Today, 2012, 193(1): 200–206 https://doi.org/10.1016/j.cattod.2012.02.003
26
Han D, Bao Z, Xing H, Yang Y, Ren Q, Zhang Z. Fabrication of plasmonic Au-Pd alloy nanoparticles for photocatalytic Suzuki-Miyaura reactions under ambient conditions. Nanoscale, 2017, 9(18): 6026–6032 https://doi.org/10.1039/C7NR01950E
27
Wilson D A, Wilson C J, Rosen B M, Percec V. Two-step, one-pot Ni-catalyzed neopentylglycolborylation and complementary Pd/Ni-catalyzed cross-coupling with aryl halides, mesylates, and tosylates. Organic Letters, 2008, 10(21): 4879–4882 https://doi.org/10.1021/ol801972f
28
Son S U, Jang Y, Park J, Na H B, Park H M, Yun H J, Lee J, Hyeon T. Designed synthesis of atom-economical Pd/Ni bimetallic nanoparticle-based catalysts for Sonogashira coupling reactions. Journal of the American Chemical Society, 2004, 126(16): 5026–5027 https://doi.org/10.1021/ja039757r
29
Heshmatpour F, Abazari R, Balalaie S. Preparation of monometallic (Pd, Ag) and bimetallic (Pd/Ag, Pd/Ni, Pd/Cu) nanoparticles via reversed micelles and their use in the Heck reaction. Tetrahedron, 2012, 68(14): 3001–3011 https://doi.org/10.1016/j.tet.2012.02.028
30
Takenaka S, Shigeta Y, Tanabe E, Otsuka K. Methane decomposition into hydrogen and carbon Nanofibers over supported Pd-Ni catalysts: Characterization of the catalysts during the reaction. Journal of Physical Chemistry B, 2004, 108(23): 7656–7664 https://doi.org/10.1021/jp0377331
31
Feng L, Chong H, Li P, Xiang J, Fu F, Yang S, Yu H, Sheng H, Zhu M. Pd-Ni alloy nanoparticles as effective catalysts for Miyaura-Heck coupling reactions. Journal of Physical Chemistry C, 2015, 119(21): 11511–11515 https://doi.org/10.1021/jp510988m
32
Xiang J, Li P, Chong H, Feng L, Fu F, Wang Z, Zhang S, Zhu M. Bimetallic Pd-Ni core-shell nanoparticles as effective catalysts for the Suzuki reaction. Nano Research, 2014, 7(9): 1337–1343 https://doi.org/10.1007/s12274-014-0498-8
33
Xia J, Fu Y, He G, Sun X, Wang X. Core-shell-like Ni-Pd nanoparticles supported on carbon black as a magnetically separable catalyst for green Suzuki-Miyaura coupling reactions. Applied Catalysis B: Environmental, 2017, 200: 39–46 https://doi.org/10.1016/j.apcatb.2016.06.066
34
Metin Ö, Ho S F, Alp C, Can H, Mankin M N, Gültekin M S, Chi M, Sun S. Ni/Pd core/shell nanoparticles supported on graphene as a highly active and reusable catalyst for Suzuki-Miyaura cross-coupling reaction. Nano Research, 2013, 6(1): 10–18 https://doi.org/10.1007/s12274-012-0276-4
35
Kim M R, Choi S H. One-step synthesis of Pd-M/ZnO (M= Ag, Cu, and Ni) catalysts by irradiation and their use in hydrogenation and Suzuki reaction. Journal of Nanomaterials, 2009, 2009: e302919
36
Kim S J, Oh S D, Lee S, Choi S H. Radiolytic synthesis of Pd-M (M= Ag, Ni, and Cu)/C catalyst and their use in Suzuki-type and Heck-type reaction. Journal of Industrial and Engineering Chemistry, 2008, 14(4): 449–456 https://doi.org/10.1016/j.jiec.2008.02.006
37
Han F S. Transition-metal-catalyzed Suzuki-Miyaura cross-coupling reactions: A remarkable advance from palladium to nickel catalysts. Chemical Society Reviews, 2013, 42(12): 5270–5298 https://doi.org/10.1039/c3cs35521g