Chemoselective Hydrogenation of Nitrobenzaldehyde to Nitrobenzyl Alcohol with Unsupported Au Nanorod Catalysts in Water

We report the chemoselective hydrogenation of 4-nitrobenaldehyde to 4-nitrobenzyl alcohol using the unsupported Au spherical nanoparticle and nanorod catalysts at 80 °C in water. A ∼100% selectivity for the 4-nitrobenzyl alcohol product was obtained when the hydrogenation reaction was catalyzed by the unsupported gold catalysts. The Au nanorod catalysts exhibited an aspect-ratio dependent reactivity and generally performed much better than the Au spherical nanoparticle catalyst. The Au nanorod catalysts showed excellent recyclability in the chemoselective hydrogenation (>99% conversion and 100% selectivity after 5 cycles).

[1]  R. Jin,et al.  Size Dependence of Atomically Precise Gold Nanoclusters in Chemoselective Hydrogenation and Active Site Structure , 2014 .

[2]  R. Jin,et al.  Thermally robust Au99(SPh)42 nanoclusters for chemoselective hydrogenation of nitrobenzaldehyde derivatives in water. , 2014, Journal of the American Chemical Society.

[3]  Rongchao Jin,et al.  Atomically precise gold nanoclusters as new model catalysts. , 2013, Accounts of chemical research.

[4]  Ming-Wei Chen,et al.  Unsupported nanoporous gold catalyst for highly selective hydrogenation of quinolines. , 2013, Organic letters.

[5]  Yong‐Gui Zhou,et al.  Homogeneous palladium-catalyzed asymmetric hydrogenation. , 2013, Chemical Society reviews.

[6]  S. J. Ambrose,et al.  Stable and recyclable Au25 clusters for the reduction of 4-nitrophenol. , 2013, Chemical communications.

[7]  Luyang Chen,et al.  Nanoporous gold catalyst for highly selective semihydrogenation of alkynes: remarkable effect of amine additives. , 2012, Journal of the American Chemical Society.

[8]  Kangnian Fan,et al.  An unusual chemoselective hydrogenation of quinoline compounds using supported gold catalysts. , 2012, Journal of the American Chemical Society.

[9]  H. Yano,et al.  N,N-Dimethylformamide-stabilized gold nanoclusters as a catalyst for the reduction of 4-nitrophenol. , 2012, Nanoscale.

[10]  Manolis Stratakis,et al.  Catalysis by supported gold nanoparticles: beyond aerobic oxidative processes. , 2012, Chemical reviews.

[11]  Robert J. Davis,et al.  Mechanistic insights on the hydrogenation of α,β-unsaturated ketones and aldehydes to unsaturated alcohols over metal catalysts , 2012 .

[12]  M. Yus,et al.  Nickel nanoparticles in hydrogen transfer reactions. , 2011, Accounts of chemical research.

[13]  A. Corma,et al.  Gold-catalyzed carbon-heteroatom bond-forming reactions. , 2011, Chemical reviews.

[14]  R. Jin,et al.  Comparison of the Catalytic Properties of 25-Atom Gold Nanospheres and Nanorods , 2011 .

[15]  J. Fletchera,et al.  A review of the use of gold catalysts in selective hydrogenation reactions Lynsey McEwana , 2010 .

[16]  R. Jin,et al.  The role of bromide ions in seeding growth of Au nanorods. , 2010, Langmuir : the ACS journal of surfaces and colloids.

[17]  R. Jin,et al.  Atomically precise Au25(SR)18 nanoparticles as catalysts for the selective hydrogenation of alpha,beta-unsaturated ketones and aldehydes. , 2010, Angewandte Chemie.

[18]  Kangnian Fan,et al.  Efficient and selective room-temperature gold-catalyzed reduction of nitro compounds with CO and H(2)O as the hydrogen source. , 2009, Angewandte Chemie.

[19]  Juan Zhang,et al.  Novel chemoselective hydrogenation of aromatic nitro compounds over ferric hydroxide supported nanocluster gold in the presence of CO and H2O. , 2009, Chemical communications.

[20]  Avelino Corma,et al.  Supported gold nanoparticles as catalysts for organic reactions. , 2008, Chemical Society reviews.

[21]  L. Prati,et al.  Selective oxidation using gold. , 2008, Chemical Society reviews.

[22]  M. Ueno,et al.  Recent advances in immobilized metal catalysts for environmentally benign oxidation of alcohols. , 2008, Chemistry, an Asian journal.

[23]  J. Fierro,et al.  A density functional theory study of the dissociation of H2 on gold clusters: importance of fluxionality and ensemble effects. , 2006, The Journal of chemical physics.

[24]  A. Corma,et al.  Chemoselective Hydrogenation of Nitro Compounds with Supported Gold Catalysts , 2006, Science.

[25]  Mostafa A. El-Sayed,et al.  Preparation and Growth Mechanism of Gold Nanorods (NRs) Using Seed-Mediated Growth Method , 2003 .

[26]  George C Schatz,et al.  What controls the melting properties of DNA-linked gold nanoparticle assemblies? , 2000, Journal of the American Chemical Society.

[27]  B. Nikoobakht,et al.  種結晶を媒介とした成長法を用いた金ナノロッド(NR)の調製と成長メカニズム , 2003 .

[28]  Catherine J. Murphy,et al.  Wet Chemical Synthesis of High Aspect Ratio Cylindrical Gold Nanorods , 2001 .

[29]  Ryoji Noyori,et al.  Asymmetric Catalysis by Architectural and Functional Molecular Engineering: Practical Chemo- and Stereoselective Hydrogenation of Ketones. , 2001, Angewandte Chemie.

[30]  P. Claus,et al.  Supported Gold Nanoparticles from Quantum Dot to Mesoscopic Size Scale: Effect of Electronic and Structural Properties on Catalytic Hydrogenation of Conjugated Functional Groups , 2000 .