Hydroformylation of alkenes over rhodium supported on the metal-organic framework ZIF-8

Nano Research

Volumn 7, Issue 9, 2014, Pages 1364-1369

  Hou, Chao ^a   Zhao, Guofeng ^a   Ji, Yongjun ^a   Niu, Zhiqiang ^a   Wang, Dingsheng ^a   Li, Yadong ^a  

^a TSINGHUA UNIVERSITY   (China)

Author keywords

catalyst; heterogeneous catalysis; hydroformylation; metal organic framework; supported rhodium; ZIF 8

Indexed keywords

EID: 84927656850     PISSN: 19980124     EISSN: 19980000     Source Type: Journal    
DOI: 10.1007/s12274-014-0501-4     Document Type: Article

References (45)

1. Franke, R.; Selent, D.; Börner, A. Applied hydroformylation. Chem. Rev.2012, 112, 5675–5732.
2. Metin, O.; Ho, S. F.; Alp, C.; Can, H.; Mankin, M. N.; Gultekin, M. S.; Chi, M. F.; Sun, S. H. Ni/Pd core/shell nanoparticles supported on graphene as a highly active and reusable catalyst for Suzuki-Miyaura cross-coupling reaction. Nano Res.2013, 6, 10–18.
3. Beller, M.; Cornils, B.; Frohning, C. D.; Kohlpaintner, C. W. Progress in hydroformylation and carbonylation. J. Mol. Catal. A: Chem.1995, 104, 17–85.
4. Chikkali, S. H.; Vlugt, J. I.; Reek, J. N. H. Hybrid diphosphorus ligands in rhodium catalysed asymmetric hydroformylation. Coord. Chem. Rev.2014, 262, 1–15.
5. Ungváry, F. Application of transition metals in hydroformylation annual survey covering the year 2006. Coord. Chem. Rev.2007, 251, 2087–2102.
6. Fernández, P. H.; Benet, B. J.; Vidal, F. A. Small bite-angle P-OP ligands for asymmetric hydroformylation and hydrogenation. Org. Lett.2013, 15, 3634–3637.
7. Selent, D.; Franke, R.; Kubis, C.; Spannenberg, A.; Baumann, W.; Kreidler, B.; Börner, A. A new diphosphite promoting highly regioselective rhodium-catalyzed hydroformylation. Organometallics2011, 30, 4509–4514.
8. Doro, F.; Reek, J. N. H.; Leeuwen, P. W. N. M. Isostructural phosphine-phosphite ligands in rhodium-catalyzed asymmetric hydroformylation. Organometallics2010, 29, 4440–4447.
9. Worthy, A. D.; Joe, C. L.; Lightburn, T. E.; Tan, K. L. Application of a chiral scaffolding ligand in catalytic enantioselective hydroformylation. J. Am. Chem. Soc.2010, 132, 14757–14759.
10. Chikkali, S. H.; Bellini, R.; Bruin, B.; Vlugt, J. I.; Reek, J. N. H. Highly selective asymmetric Rh-catalyzed hydroformylation of heterocyclic olefins. J. Am. Chem. Soc.2012, 134, 6607–6616.
11. Wang, X.; Buchwald, S. L. Rh-catalyzed asymmetric hydroformylation of functionalized 1,1-disubstituted olefins. J. Am. Chem. Soc.2011, 133, 19080–19083.
12. Lightburn, T. E.; Paolis, O. A. D.; Cheng, K. H.; Tan, K. L. Regioselective hydroformylation of allylic alcohols. Org. Lett.2011, 13, 2686–2689.
13. Chen, C.; Qiao, Y.; Geng, H.; Zhang, X. A novel triphosphoramidite ligand for highly regioselective linear hydroformylation of terminal and internal olefins. Org. Lett.2013, 15, 1048–1051.
14. Dabbawala, A. A.; Bajaj, H. C.; Jasra, R. V. Rhodium complex of monodentate phosphite as a catalyst for olefins hydroformylation. J. Mol. Catal. A: Chem.2009, 302, 97–106.
15. Yoneda, N.; Nakagawa, Y.; Mimami, T. Hydroformylation catalyzed by immobilized rhodium complex to polymer support. Catal. Today1997, 36, 357–364.
16. Huang, L.; He, Y.; Kawi, S. Catalytic studies of aminated MCM-41-tethered rhodium complexes for hydroformylation of 1-octene and styrene. J. Mol. Catal. A: Chem.2004, 213, 241–249.
17. Riisager, A.; Wasserscheid, P.; Hal, R.; Fehrmann, R. Continuous fixed-bed gas-phase hydroformylation using supported ionic liquid-phase (SILP) Rh catalysts. J. Catal.2003, 219, 452–455.
18. Zhang, Y.; Nagasaka, K.; Qiu, X.; Tsubaki, N. Low-pressure hydroformylation of 1-hexene over active carbon-supported noble metal catalysts. Appl. Catal. A: Gen.2004, 276, 103–111.
19. Zhou, W.; He, D. A facile method for promoting activities of ordered mesoporous silica-anchored Rh-P complex catalysts in 1-octene hydroformylation. Green Chem.2009, 11, 1146–1154.
20. Zhou, W.; He, D. Lengthening alkyl spacers to increase SBA-15-anchored Rh-P complex activities in 1-octene hydroformylation. Chem. Commun.2008, 5839–5841.
21. 3 complex in hydrotalcite. J. Mol. Catal. A: Chem.2010, 316, 153–162.
22. Liu, N. A.; Yao, Y.; Cha, J. J.; McDowell, M. T.; Han, Y.; Cui, Y. Functionalization of silicon nanowire surfaces with metal-organic frameworks. Nano Res.2012, 5, 109–116.
23. Paz, F. A. A.; Klinowski, J.; Vilela, S. M. F.; Tomé, J. P. C.; Cavaleiro, J. A. S.; Rocha, J. Ligand design for functional metal-organic frameworks. Chem. Soc. Rev.2012, 41, 1088–1110.
24. Cohen, S. M. Postsynthetic methods for the functionalization of metal-organic frameworks. Chem. Rev.2012, 112, 970–1000.
25. O’Keeffe, M.; Yaghi, O. M. Deconstructing the crystal structures of metal-organic frameworks and related materials into their underlying nets. Chem. Rev.2012, 112, 675–702.
26. Cook, T. R.; Zheng, Y. R.; Stang, P. J. Metal-organic frameworks and self-assembled supramolecular coordination complexes: Comparing and contrasting the design, synthesis, and functionality of metal-organic materials. Chem. Rev.2013, 113, 734–777.
27. El-Shall, M. S.; Abdelsayed, V.; Khder, A. S.; Hassan, H. A.; El-Kaderi, H. M.; Reich, T. E. Metallic and bimetallic nanocatalysts incorporated into highly porous coordination polymer MIL-101. J. Mater. Chem.2009, 19, 7625–7631.
28. Jiang, H. L.; Akita, T.; Ishida, T.; Haruta, M.; Xu, Q. Synergistic catalysis of Au@Ag core-shell nanoparticles stabilized on metal-organic framework. J. Am. Chem. Soc.2011, 133, 1304–1306.
29. Yuan, B. Z.; Pan, Y. Y.; Li, Y. W.; Yin, B. L.; Jiang, H. F. A highly active heterogeneous palladium catalyst for the Suzuki-Miyaura and Ullmann coupling reactions of aryl chlorides in aqueous media. Angew. Chem. Int. Ed.2010, 49, 4054–4508.
30. 3] by hydrogenolysis of adsorbed [Ru(cod)(cot)]: A solid-state reference system for surfactant-stabilized ruthenium colloids. J. Am. Chem. Soc.2008, 130, 6119–6130.
31. Dhakshinamoorthy, A.; Garcia, H. Catalysis by metal nanoparticles embedded on metal-organic frameworks. Chem. Soc. Rev.2012, 41, 5262–5284.
32. Moon, H. R.; Lim, D. W.; Suh, M. P. Fabrication of metal nanoparticles in metal-organic frameworks. Chem. Soc. Rev.2013, 42, 1807–1824.
33. Zhu, Q. L.; Li, J.; Xu, Q. Immobilizing metal nanoparticles to metal-organic frameworks with size and location control for optimizing catalytic performance. J. Am. Chem. Soc.2013, 135, 10210–10213.
34. Zahmakiran, M. Iridium nanoparticles stabilized by metal organic frameworks (IrNPs@ZIF-8): Synthesis, structural properties and catalytic performance. Dalton. Trans.2012, 41, 12690–12696.
35. Huang, X. C.; Lin, Y. Y.; Zhang, J. P.; Chen, X. M. Ligand-directed strategy for zeolite-type metal-organic frameworks: Zinc(II) imidazolates with unusual zeolitic topologies. Angew. Chem. Int. Ed.2006, 45, 1557–1559.
36. Park, K. S.; Ni, Z.; Cote, A. P.; Choi, J. Y.; Huang, R. D.; Uribe-Romo, F. J.; Chae, H. K.; O’Keeffe, M.; Yaghi, O. M. Exceptional chemical and thermal stability of zeolitic imidazolate frameworks. Proc. Natl. Acad. Sci. USA2006, 103, 10186–10191.
37. Jiang, H. L.; Liu, B.; Akita, T.; Haruta, M.; Sakurai, H.; Xu, Q. Au@ZIF-8: CO oxidation over gold nanoparticles deposited to metal-organic framework. J. Am. Chem. Soc.2009, 131, 11302–1303.
38. Wang, P.; Zhao, J.; Li, X.; Yang, Y.; Yang, Q.; Li, C. Assembly of ZIF nanostructures around free Pt nanoparticles: Efficient size-selective catalysts for hydrogenation of alkenes under mild conditions. Chem. Commun.2013, 49, 3330–3332.
39. Li, P. Z.; Aranishi, K.; Xu, Q. ZIF-8 immobilized nickel nanoparticles: Highly effective catalysts for hydrogen generation from hydrolysis of ammonia borane. Chem. Commun.2012, 48, 3173–3175.
40. Hermannsdörfer, J.; Kempe, R. Selective palladium-loaded MIL-101 catalysts. Chem. Eur. J.2011, 17, 8071–8077.
41. Bruss, A. J.; Gelesky, M. A.; Machado, G.; Dupont, J. Rh(0) nanoparticles as catalyst precursors for the solventless hydroformylation of olefins. J. Mol. Catal. A: Chem.2006, 252, 212–218.
42. Vu, T. V.; Kosslick, H.; Schulz, A.; Harloff, J.; Paetzold, E.; Schneider, M.; Radnik, J.; Steinfeldt, N.; Fulda, G.; Kragl, U. Selective hydroformylation of olefins over the rhodium supported large porous metal-organic framework MIL-101. Appl. Catal. A: Gen.2013, 468, 410–417.
43. Vu, T. V.; Kosslick, H.; Schulz, A.; Harloff, J.; Paetzold, E.; Schneider, M.; Radnik, J.; Kragl, U.; Fulda, G.; Janiak, C.; Tuyen, N. D. Hydroformylation of olefins over rhodium supported metal-organic framework catalysts of different structure. Micropor. Mesopor. Mater.2013, 177, 135–142.
44. Zeng, Y.; Wang, Y.; Jiang, J.; Jin, Z. Rh nanoparticle catalyzed hydrogenation of olefins in thermoregulated ionic liquid and organic biphase system. Catal. Commun.2012, 19, 70–73.
45. Sun, Z.; Wang, Y.; Niu, M.; Yi, H.; Jiang, J.; Jin, Z. Poly(ethylene glycol)-stabilized Rh nanoparticles as efficient and recyclable catalysts for hydroformylation of olefins. Catal. Commun.2012, 27, 78–82.