Silver Nanoparticles Supported by Novel Nickel Metal-Organic Frameworks: An Efficient Heterogeneous Catalyst for an A^³ Coupling Reaction

Abstract

A novel heterogeneous catalyst of silver nanoparticles was prepared by using a nickel metal-organic framework (Ni-MOF) as a template. The catalyst has a very high catalytic activity and a strict structural selectivity towards linear aliphatic aldehydes in an A^³ coupling reaction. The catalyst could be recovered by simple phase separation and reused for many times without obvious loss of activity.

silver nanoparticles - template - metal-organic frameworks - heterogeneous catalyst - A^³ coupling

References and Notes

1a Hermes S. Schröder F. Chelmowski R. Wöll C. Fischer R. J. Am. Chem. Soc.  2005,  127:  13744 

1b Hermes S. Schröter M. Schmid R. Khodeir L. Muhler M. Tissler A. Fischer RW. Fischer RA. Angew. Chem. Int. Ed.  2005,  44:  6237 

1c Suh MP. Moon HR. Lee EY. Jang SY. J. Am. Chem. Soc.  2006,  128:  4710 

1d Moon HR. Kim JH. Suh MP. Angew. Chem. Int. Ed.  2005,  44:  1261 

1e Tanaka D. Kitagawa S. Chem. Mater.  2008,  20:  922 

1f Cheon YE. Suh MP. Chem. Eur. J.  2008,  14:  3916 

2a Okamoto K. Akiyama R. Yoshida H. Yoshida T. Kobayashi S. J. Am. Chem. Soc.  2005,  127:  2125 

2b Ooe M. Murata M. Mizugaki T. Ebitani K. Kaneda K. J. Am. Chem. Soc.  2004,  126:  1604 

2c Garcia-Martinez JC. Lezutekong R. Crooks RM. J. Am. Chem. Soc.  2005,  127:  5097 

2d Huang J. Jiang T. Gao H. Han B. Liu Z. Wu W. Chang Y. Zhao G. Angew. Chem. Int. Ed.  2004,  43:  1397 

3a Wang ZX. Chen M. Wu LM. Chem. Mater.  2008,  20:  3251 

3b Dong YB. Xu HX. Ma JP. Huang RQ. Inorg. Chem.  2006,  45:  3325 

3c Hiraoka S. Tanaka T. Shionoya M. J. Am. Chem. Soc.  2006,  128:  13038 

3d Chattopadhyay S. Shi SC. Lan ZH. Chen CF. Chen K. Chen LC. J. Am. Chem. Soc.  2005,  127:  2820 

3e Berti L. Alessandrini A. Facci P. J. Am. Chem. Soc.  2005,  127:  11216 

4 X-ray diffraction data of Ni-MOF were collected on a Bruker SMART APEX II CCD diffractometer equipped with a graphite crystal and incident beam monochromator using Mn Kα radiation (λ = 0.71073 Å) at 293 K. The structure was solved by direct method. Crystallographic Parameters C₄₀H₃₄N₄Ni₂O₁₃S₆, M = 1088.49, monoclinic, space group C2/c, a = 22.7475, b = 19.5874, c = 12.0742 Å, α = 90.000˚, β = 99.593˚, γ = 90.000˚, V = 5304.318 Å^³, Z = 4, D _c = 1.363 g/cm^³, F(000) = 2232, µ = 1.004 mm^-¹, crystal size: 0.161 × 0.088 × 0.066, goodness of fit: 0.914, R ₁[I > 2σ(I)] = 0.0677, wR ₂[I > 2σ(I)] = 0.1742, R ₁ (all data) = 0.1275, wR ₂ (all data) = 0.2036, residuals (e Å^-³): 0.546, -0.648. CCDC 675102

5 Frey J. Proemmel S. Armitage MA. Holmes AB. Org. Synth.  2006,  83:  209 

6 Raveendran P. Fu J. Wallen SL. J. Am. Chem. Soc.  2003,  125:  13940 

7 Kobayashi Y. Salgueiriño-Maceira V. Liz-Marzán LM. Chem. Mater.  2001,  13:  1630 

8a Zhang Y. Santos AM. Herdtweck E. Mink J. Kuhn FE. New J. Chem.  2005,  29:  366 

8b Wei C. Li Z. Li CJ. Org. Lett.  2003,  5:  4473 

8c Li Z. Wei C. Chen L. Varma RS. Li CJ. Tetrahedron Lett.  2004,  45:  2443 

8d Wei C. Li Z. Li CJ. Synlett  2004,  1472 

8e Wei C. Li CJ. J. Am. Chem. Soc.  2003,  125:  9584 

8f Lo VK. Liu Y. Wong M. Che C. Org. Lett.  2006,  8:  1529 

8g Shi L. Tu Y. Wang M. Zhang F. Fan C. Org. Lett.  2004,  6:  1001 

8h Kabalka GW. Wang L. Pagni RM. Synlett  2001,  676 

8i Fischer C. Carreira EM. Org. Lett.  2001,  3:  4319 

8j Wei C. Li CJ. Chem. Commun.  2002,  268 

9

General Procedure for the A ^³ Coupling Reaction To a solution of aldehyde (1.0 mmol) and amine (1.2 mmol) in MeCN (5.0 mL) was added a certain loading of catalyst (5.0 mg). Then the mixture was degassed in vacuum and put into a nitrogen atmosphere. After adding alkyne (1.5 mmol) into the mixture, it was heated at 70-80 ˚C for a required reaction time. Then the solid phase was filtered off and residue solvent was evaporated under vacuum. Product was obtained after purification by column chromatography.

10 SHELXL97. Program for the Solution of Crystal Structures   Sheldrick GM. University of Göttingen; Germany: 1997.