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

<A NAME="RW14908ST-1A">1a</A> Hermes S. Schröder F. Chelmowski R. Wöll C. Fischer R. J. Am. Chem. Soc.  2005,  127:  13744 

<A NAME="RW14908ST-1B">1b</A> Hermes S. Schröter M. Schmid R. Khodeir L. Muhler M. Tissler A. Fischer RW. Fischer RA. Angew. Chem. Int. Ed.  2005,  44:  6237 

<A NAME="RW14908ST-1C">1c</A> Suh MP. Moon HR. Lee EY. Jang SY. J. Am. Chem. Soc.  2006,  128:  4710 

<A NAME="RW14908ST-1D">1d</A> Moon HR. Kim JH. Suh MP. Angew. Chem. Int. Ed.  2005,  44:  1261 

<A NAME="RW14908ST-1E">1e</A> Tanaka D. Kitagawa S. Chem. Mater.  2008,  20:  922 

<A NAME="RW14908ST-1F">1f</A> Cheon YE. Suh MP. Chem. Eur. J.  2008,  14:  3916 

<A NAME="RW14908ST-2A">2a</A> Okamoto K. Akiyama R. Yoshida H. Yoshida T. Kobayashi S. J. Am. Chem. Soc.  2005,  127:  2125 

<A NAME="RW14908ST-2B">2b</A> Ooe M. Murata M. Mizugaki T. Ebitani K. Kaneda K. J. Am. Chem. Soc.  2004,  126:  1604 

<A NAME="RW14908ST-2C">2c</A> Garcia-Martinez JC. Lezutekong R. Crooks RM. J. Am. Chem. Soc.  2005,  127:  5097 

<A NAME="RW14908ST-2D">2d</A> Huang J. Jiang T. Gao H. Han B. Liu Z. Wu W. Chang Y. Zhao G. Angew. Chem. Int. Ed.  2004,  43:  1397 

<A NAME="RW14908ST-3A">3a</A> Wang ZX. Chen M. Wu LM. Chem. Mater.  2008,  20:  3251 

<A NAME="RW14908ST-3B">3b</A> Dong YB. Xu HX. Ma JP. Huang RQ. Inorg. Chem.  2006,  45:  3325 

<A NAME="RW14908ST-3C">3c</A> Hiraoka S. Tanaka T. Shionoya M. J. Am. Chem. Soc.  2006,  128:  13038 

<A NAME="RW14908ST-3D">3d</A> Chattopadhyay S. Shi SC. Lan ZH. Chen CF. Chen K. Chen LC. J. Am. Chem. Soc.  2005,  127:  2820 

<A NAME="RW14908ST-3E">3e</A> Berti L. Alessandrini A. Facci P. J. Am. Chem. Soc.  2005,  127:  11216 

<A NAME="RW14908ST-4">4</A> 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

<A NAME="RW14908ST-5">5</A> Frey J. Proemmel S. Armitage MA. Holmes AB. Org. Synth.  2006,  83:  209 

<A NAME="RW14908ST-6">6</A> Raveendran P. Fu J. Wallen SL. J. Am. Chem. Soc.  2003,  125:  13940 

<A NAME="RW14908ST-7">7</A> Kobayashi Y. Salgueiriño-Maceira V. Liz-Marzán LM. Chem. Mater.  2001,  13:  1630 

<A NAME="RW14908ST-8A">8a</A> Zhang Y. Santos AM. Herdtweck E. Mink J. Kuhn FE. New J. Chem.  2005,  29:  366 

<A NAME="RW14908ST-8B">8b</A> Wei C. Li Z. Li CJ. Org. Lett.  2003,  5:  4473 

<A NAME="RW14908ST-8C">8c</A> Li Z. Wei C. Chen L. Varma RS. Li CJ. Tetrahedron Lett.  2004,  45:  2443 

<A NAME="RW14908ST-8D">8d</A> Wei C. Li Z. Li CJ. Synlett  2004,  1472 

<A NAME="RW14908ST-8E">8e</A> Wei C. Li CJ. J. Am. Chem. Soc.  2003,  125:  9584 

<A NAME="RW14908ST-8F">8f</A> Lo VK. Liu Y. Wong M. Che C. Org. Lett.  2006,  8:  1529 

<A NAME="RW14908ST-8G">8g</A> Shi L. Tu Y. Wang M. Zhang F. Fan C. Org. Lett.  2004,  6:  1001 

<A NAME="RW14908ST-8H">8h</A> Kabalka GW. Wang L. Pagni RM. Synlett  2001,  676 

<A NAME="RW14908ST-8I">8i</A> Fischer C. Carreira EM. Org. Lett.  2001,  3:  4319 

<A NAME="RW14908ST-8J">8j</A> Wei C. Li CJ. Chem. Commun.  2002,  268 

<A NAME="RW14908ST-9">9</A>

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.

<A NAME="RW14908ST-10">10</A> SHELXL97. Program for the Solution of Crystal Structures   Sheldrick GM. University of Göttingen; Germany: 1997.