Palladium nanocrystals stabilized by cucurbit[6]uril as efficient heterogeneous catalyst for direct C-H functionalization of polyfluoroarenes

Journal of Catalysis

Volumn 321, Issue , 2015, Pages 62-69

  Cao, Minna ^a   Wu, Dongshuang ^a   Su, Weiping ^a   Cao, Rong ^a  

^a FUJIAN INSTITUTE OF RESEARCH ON THE STRUCTURE OF MATTER   (China)

Author keywords

C H functionalization; Cucurbit 6 uril; Heterogeneous; Nanocrystals; Palladium

Indexed keywords

CATALYSTS; NANOCRYSTALS; PALLADIUM; SURFACE DEFECTS;

AMBIENT ENVIRONMENT; C-H FUNCTIONALIZATION; CATALYST LOADINGS; CATALYTIC MECHANISMS; CUCURBIT[6]URIL; ELECTRON-DEFICIENT; HETEROGENEOUS; HETEROGENEOUS CATALYST;

CATALYST ACTIVITY;

EID: 84925958922     PISSN: 00219517     EISSN: 10902694     Source Type: Journal    
DOI: 10.1016/j.jcat.2014.10.013     Document Type: Article

References (44)

1. M. Lafrance, C.N. Rowley, T.K. Woo, and K. Fagnou Catalytic intermolecular direct arylation of perfluorobenzenes J. Am. Chem. Soc. 128 2006 8754 8756
2. J.J. Mousseau, and A.B. Charette Direct functionalization processes: a journey from palladium to copper to iron to nickel to metal-free coupling reactions Acc. Chem. Res. 46 2013 412 424
3. L. Ackermann, R. Vicente, and A.R. Kapdi Transition-metal-catalyzed direct arylation of (hetero)arenes by C-H bond cleavage Angew. Chem. Int. Ed. 48 2009 9792 9826
4. D. Alberico, M.E. Scott, and M. Lautens Aryl-aryl bond formation by transition-metal-catalyzed direct arylation Chem. Rev. 107 2007 174 238
5. L.G. Mercier, and M. Leclerc Direct (Hetero) arylation: a new tool for polymer chemists Acc. Chem. Res. 2013
6. M. Miura, and M. Nomura Direct arylation via cleavage of activated and unactivated C-H bonds N. Miyaura, Cross-Coupling Reactions 2002 Springer Berlin Heidelberg 211 241
7. W. Liu, F. Tian, X. Wang, H. Yu, and Y. Bi Simple alcohols promoted direct C-H arylation of unactivated arenes with aryl halides Chem. Commun. 49 2013 2983 2985
8. D.G. Yu, X. Wang, R.Y. Zhu, S. Luo, X.B. Zhang, B.Q. Wang, L. Wang, and Z.J. Shi Direct arylation/alkylation/magnesiation of benzyl alcohols in the presence of Grignard reagents via Ni-, Fe-, or Co-catalyzed sp3 C-O bond activation J. Am. Chem. Soc. 134 2012 14638 14641
9. L.L. Chng, N. Erathodiyil, and J.Y. Ying Nanostructured catalysts for organic transformations Acc. Chem. Res. 46 2013 1825 1837
10. H. Miyamura, and S. Kobayashi Tandem oxidative processes catalyzed by polymer-incarcerated multimetallic nanoclusters with molecular oxygen Acc. Chem. Res. 47 2014 1054 1066
11. T. Yasukawa, H. Miyamura, and S. Kobayashi Polymer-incarcerated chiral Rh/Ag nanoparticles for asymmetric 1,4-addition reactions of arylboronic acids to enones: remarkable effects of bimetallic structure on activity and metal leaching J. Am. Chem. Soc. 134 2012 16963 16966
12. M. Sankar, N. Dimitratos, P.J. Miedziak, P.P. Wells, C.J. Kiely, and G.J. Hutchings Designing bimetallic catalysts for a green and sustainable future Chem. Soc. Rev. 41 2012 8099 8139
13. M.A. Mahmoud, R. Narayanan, and M.A. El-Sayed Enhancing colloidal metallic nanocatalysis: sharp edges and corners for solid nanoparticles and cage effect for hollow ones Acc. Chem. Res. 46 2013 1795 1805
14. R. Narayanan, and M.A. El-Sayed Effect of colloidal nanocatalysis on the metallic nanoparticle shape: the Suzuki reaction Langmuir 21 2005 2027 2033
15. R.V. Jagadeesh, A.E. Surkus, H. Junge, M.M. Pohl, J. Radnik, J. Rabeah, H. Huan, V. Schunemann, A. Bruckner, and M. Beller Nanoscale Fe2O3-based catalysts for selective hydrogenation of nitroarenes to anilines Science 342 2013 1073 1076
16. F.A. Westerhaus, R.V. Jagadeesh, G. Wienhofer, M.M. Pohl, J. Radnik, A.E. Surkus, J. Rabeah, K. Junge, H. Junge, M. Nielsen, A. Bruckner, and M. Beller Heterogenized cobalt oxide catalysts for nitroarene reduction by pyrolysis of molecularly defined complexes Nat. Chem. 5 2013 537 543
17. F. Shi, M.K. Tse, S. Zhou, M.M. Pohl, J. Radnik, S. Hubner, K. Jahnisch, A. Bruckner, and M. Beller Green and efficient synthesis of sulfonamides catalyzed by nano-Ru/Fe(3)O(4) J. Am. Chem. Soc. 131 2009 1775 1779
18. S. Noel, B. Leger, A. Ponchel, K. Philippot, A. Denicourt-Nowicki, A. Roucoux, and E. Monflier Cyclodextrin-based systems for the stabilization of metallic (0) nanoparticles and their versatile applications in catalysis Catal. Today 235 2014 20 32
19. M.V. Rekharsky, and Y. Inoue Complexation thermodynamics of cyclodextrins Chem. Rev. 98 1998 1875 1918
20. F. Hapiot, A. Ponchel, S. Tilloy, and E. Monflier Cyclodextrins and their applications in aqueous-phase metal-catalyzed reactions C.R. Chim. 14 2011 149 166
21. M. Zhao, K. Deng, L. He, Y. Liu, G. Li, H. Zhao, and Z. Tang Core-shell palladium nanoparticle@metal-organic frameworks as multifunctional catalysts for cascade reactions J. Am. Chem. Soc. 136 2014 1738 1741
22. C.K. Tsung, J.N. Kuhn, W. Huang, C. Aliaga, L.I. Hung, G.A. Somorjai, and P. Yang Sub-10 nm platinum nanocrystals with size and shape control: catalytic study for ethylene and pyrrole hydrogenation J. Am. Chem. Soc. 131 2009 5816 5822
23. Y. Wu, D. Wang, P. Zhao, Z. Niu, Q. Peng, and Y. Li Monodispersed Pd-Ni nanoparticles: composition control synthesis and catalytic properties in the Miyaura-Suzuki reaction Inorg. Chem. 50 2011 2046 2048
24. Z. Niu, Q. Peng, Z. Zhuang, W. He, and Y. Li Evidence of an oxidative-addition-promoted Pd-leaching mechanism in the Suzuki reaction by using a Pd-nanostructure design Chem. Eur. J. 18 2012 9813 9817
25. M. Korzec, P. Bartczak, A. Niemczyk, J. Szade, M. Kapkowski, P. Zenderowska, K. Balin, J. Lelatko, and J. Polanski Bimetallic nano-Pd/PdO/Cu system as a highly effective catalyst for the Sonogashira reaction J. Catal. 313 2014 1 8
26. D.T. Tang, K.D. Collins, J.B. Ernst, and F. Glorius Pd/C as a catalyst for completely regioselective C-H functionalization of thiophenes under mild conditions Angew. Chem. Int. Ed. 53 2014 1809 1813
27. D.T. Tang, K.D. Collins, and F. Glorius Completely regioselective direct C-H functionalization of benzo[b]thiophenes using a simple heterogeneous catalyst J. Am. Chem. Soc. 135 2013 7450 7453
28. D. Bardelang, K.A. Udachin, D.M. Leek, and J.A. Ripmeester Highly symmetric columnar channels in metal-free cucurbit[n]uril hydrate crystals (n = 6, 8) CrystEngComm 9 2007 973 975
29. M. Cao, J. Lin, H. Yang, and R. Cao Facile synthesis of palladium nanoparticles with high chemical activity using cucurbit[6]uril as protecting agent Chem. Commun. 46 2010 5088 5090
30. M. Cao, D. Wu, S. Gao, and R. Cao Platinum nanoparticles stabilized by cucurbit[6]uril with enhanced catalytic activity and excellent poisoning tolerance for methanol electrooxidation Chemistry 18 2012 12978 12985
31. T.C. Lee, and O.A. Scherman Formation of dynamic aggregates in water by cucurbit[5]uril capped with gold nanoparticles Chem. Commun. (Camb.) 46 2010 2438 2440
32. T.C. Lee, and O.A. Scherman A facile synthesis of dynamic supramolecular aggregates of cucurbit[n]uril (n = 5-8) capped with gold nanoparticles in aqueous media Chemistry 18 2012 1628 1633
33. H. Zhang, M. Jin, Y. Xiong, B. Lim, and Y. Xia Shape-controlled synthesis of Pd nanocrystals and their catalytic applications Acc. Chem. Res. 46 2013 1783 1794
34. B.C. Pemberton, R. Raghunathan, S. Volla, and J. Sivaguru From containers to catalysts: supramolecular catalysis within cucurbiturils Chemistry 18 2012 12178 12190
35. J.W. Lee, S. Samal, N. Selvapalam, H.J. Kim, and K. Kim Cucurbituril homologues and derivatives: new opportunities in supramolecular chemistry Acc. Chem. Res. 36 2003 621 630
36. A. Denicourt-Nowicki, A. Roucoux, F. Wyrwalski, N. Kania, E. Monflier, and A. Ponchel Carbon-supported ruthenium nanoparticles stabilized by methylated cyclodextrins: a new family of heterogeneous catalysts for the gas-phase hydrogenation of arenes Chem. Eur. J. 14 2008 8090 8093
37. S.S. Soomro, F.L. Ansari, K. Chatziapostolou, and K. Köhler Palladium leaching dependent on reaction parameters in Suzuki-Miyaura coupling reactions catalyzed by palladium supported on alumina under mild reaction conditions J. Catal. 273 2010 138 146
38. K. Köhler, R.G. Heidenreich, S.S. Soomro, and S.S. Pröckl Supported palladium catalysts for Suzuki reactions: structure-property relationships, optimized reaction protocol and control of palladium leaching Adv. Synth. Catal. 350 2008 2930 2936
39. S.P. Andrews, A.F. Stepan, H. Tanaka, S.V. Ley, and M.D. Smith Heterogeneous or homogeneous? A case study involving palladium-containing perovskites in the Suzuki reaction Adv. Synth. Catal. 347 2005 647 654
40. C. Deraedt, and D. Astruc "Homeopathic" palladium nanoparticle catalysis of cross carbon-carbon coupling reactions Acc. Chem. Res. 47 2014 494 503
41. X. Guo, G. Fang, G. Li, H. Ma, H. Fan, L. Yu, C. Ma, X. Wu, D. Deng, M. Wei, D. Tan, R. Si, S. Zhang, J. Li, L. Sun, Z. Tang, X. Pan, and X. Bao Direct, nonoxidative conversion of methane to ethylene, aromatics, and hydrogen Science 344 2014 616 619
42. G.A. Somorjai Modern surface science and surface technologies: an introduction Chem. Rev. 96 1996 1223 1236
43. M. Brun, A. Berthet, and J.C. Bertolini XPS, AES and Auger parameter of Pd and PdO J. Electron Spectrosc. Relat. Phenom. 104 1999 55 60
44. A. Gniewek, A.M. Trzeciak, J.J. Ziółkowski, L. Kępiński, J. Wrzyszcz, and W. Tylus Pd-PVP colloid as catalyst for Heck and carbonylation reactions: TEM and XPS studies J. Catal. 229 2005 332 343