Nano Cu-catalyzed efficient and selective reduction of nitroarenes under combined microwave and ultrasound irradiation

Clark JH: Green chemistry: challenges and opportunities. Green Chem. 1999, 1: 1-8. 10.1039/a807961g. Li CJ, Anastas PT: Green Chemistry: present and future. Chem Soc Rev. 2012, 41: 1413-1414. 10.1039/c1cs90064a. Appukkuttan P, Mehtaa VP, Van der Eycken EV: Microwave-assisted cycloaddition reactions. Chem Soc Rev. 2010, 39: 1467-1477. 10.1039/b815717k. Kappe CO, Van der Eycken EV: Click chemistry under non-classical reaction conditions. Chem Soc Rev. 2010, 39: 1280-1290. 10.1039/b901973c. Cracotto G, Cintas P: Power ultrasound in organic synthesis: moving cavitational chemistry from academia to innovative and large-scale applications. Chem Soc Rev. 2006, 35: 180-196. 10.1039/b503848k. Polshettiwar V, Varma RS: Microwave-Assisted Organic Synthesis and Transformations using Benign Reaction Media. Acc Chem Res. 2008, 41: 629-639. 10.1021/ar700238s. Tafesh AM, Weiguny J: A Review of the Selective Catalytic Reduction of Aromatic Nitro Compounds into Aromatic Amines, Isocyanates, Carbamates, and Ureas Using CO. Chem Rev. 1996, 96: 2035-2052. 10.1021/cr950083f. Li F, Cui JN, Qian XH, Zhang R, Xiao Y: Highly chemoselective reduction of aromatic nitro compounds to the corresponding hydroxylamines catalysed by plant cells from a grape. Chem Commun. 2005, 43: 1901-1903. He DP, Shi H, Wu Y, Xu BX: Synthesis of chloroanilines: selective hydrogenation of the nitro in chloronitrobenzenes over zirconia-supported gold catalyst. Green Chem. 2007, 9: 849-951. 10.1039/b618367k. Liang M, Wang X, Liu H, Wang J: Excellent catalytic properties over nanocomposite catalysts for selective hydrogenation of halonitrobenzenes. J Catal. 2008, 255: 335-342. 10.1016/j.jcat.2008.02.025. Chandrasekhar S, Prakash SJ, Rao CL: Poly(ethylene Glycol) (400) as Superior Solvent Medium against Ionic Liquids for Catalytic Hydrogenations with PtO2. J Org Chem. 2006, 71: 2196-2199. 10.1021/jo052604x. Shi Q, Lu R, Lu L, Fu X, Zhao D: Efficient Reduction of Nitroarenes over Nickel-Iron Mixed Oxide Catalyst Prepared from a Nickel-Iron Hydrotalcite Precursor. Adv Synth Catal. 2007, 349: 1877-1881. 10.1002/adsc.200700070. Mandal PK, McMurray JS: Pd − C-Induced Catalytic Transfer Hydrogenation with Triethylsilane. J Org Chem. 2007, 72: 6599-6601. 10.1021/jo0706123. Rahaim RJ, Maleczka REJ: Pd-Catalyzed Silicon Hydride Reductions of Aromatic and Aliphatic Nitro Groups. Org Lett. 2005, 7: 5087-5090. 10.1021/ol052120n. Wienhöfer G, Sorribes I, Boddien A, Westerhaus F, Junge K, Junge H, Llusar R, Beller M: General and Selective Iron-Catalyzed Transfer Hydrogenation of Nitroarenes without Base. J Am Chem Soc. 2011, 133: 12875-12879. 10.1021/ja2061038. Sharma U, Kumar P, Kumar N, Kumar V, Singh B: Highly Chemo- and Regioselective Reduction of Aromatic Nitro Compounds Catalyzed by Recyclable Copper(II) as well as Cobalt(II) Phthalocyanines. Adv Synth Catal. 2010, 352: 1834-1840. 10.1002/adsc.201000191. Song XY, Sun SX, Zhang WM, Yin ZL: A method for the synthesis of spherical copper nanoparticles in the organic phase. J Colloid Interface Sci. 2004, 273: 463-469. 10.1016/j.jcis.2004.01.019. Mitudome T, Arita S, Mori H, Mizugaki T, Jitsukawa K, Kaneda K: Supported Silver-Nanoparticle-Catalyzed Highly Efficient Aqueous Oxidation of Phenylsilanes to Silanols. Angew Chem Int Ed. 2008, 47: 7938-7940. 10.1002/anie.200802761. Min KI, Choi JS, Chung YM, Ahn WS, Ryoo R, Lim PK: p-Aminophenol synthesis in an organic/aqueous system using Pt supported on mesoporous carbons. Appl Catal A Gen. 2008, 337: 97-140. 10.1016/j.apcata.2007.12.004. Takasaki M, Motoyama Y, Higashi K, Yoon SH, Mochida I, Nagashima H: Chemoselective Hydrogenation of Nitroarenes with Carbon Nanofiber-Supported Platinum and Palladium Nanoparticles. Org Lett. 2008, 10: 1601-1604. 10.1021/ol800277a. Wang F, Liu JH, Xu XL: Layered material γ-ZrP supported platinum catalyst for liquid-phase reaction: a highly active and selective catalyst for hydrogenation of the nitro group in para-chloronitrobenzene. Chem Commun. 2008, 46: 2040-2042. Motoyamal Y, Lee YJ, Tsuji K, Yoon SH, Mochida I, Nagashima H: Platinum Nanoparticles Supported on Nitrogen-doped Carbon Nanofibers as Efficient Poisoning Catalysts for the Hydrogenation of Nitroarenes. ChemCatChem. 2011, 3: 1578-1581. 10.1002/cctc.201100135. Liu MH, Yu WY, Liu HF: Selective hydrogenation of o-chloronitrobenzene over polymer-stabilized ruthenium colloidal catalysts. J Mol Catal A Chem. 1999, 138: 295-303. 10.1016/S1381-1169(98)00159-9. Boronat P, Concepción A, Corma S, González F, Serna IP: A Molecular Mechanism for the Chemoselective Hydrogenation of Substituted Nitroaromatics with Nanoparticles of Gold on TiO2 Catalysts: A Cooperative Effect between Gold and the Support. J Am Chem Soc. 2007, 129: 16230-16237. 10.1021/ja076721g. Lou XB, He L, Qian Y, Liu YM, Cao Y, Fan KN: Highly Chemo- and Regioselective Transfer Reduction of Aromatic Nitro Compounds using Ammonium Formate Catalyzed by Supported Gold Nanoparticles. Adv Synth Catal. 2011, 353: 281-286. 10.1002/adsc.201000621. Corma A, Serna P: Chemoselective Hydrogenation of Nitro Compounds with Supported Gold Catalysts. Science. 2006, 313: 332-334. 10.1126/science.1128383. Luo PF, Xu KL, Zhang R, Huang L, Wang J, Xing WH, Huang J: Highly efficient and selective reduction of nitroarenes with hydrazine over supported rhodium nanoparticles. Catal Sci Technol. 2012, 2: 301-304. 10.1039/c1cy00358e. Pradhan N, Pal A, Pal T: Catalytic Reduction of Aromatic Nitro Compounds by Coinage Metal Nanoparticles. Langmuir. 2001, 17: 1800-1802. 10.1021/la000862d. Wen HL, Yao KS, Zhang YD, Zhou ZM, Kirschning A: Catalytic transfer hydrogenation of aromatic nitro compounds in presence of polymer-supported nano-amorphous Ni–B catalyst. Catal Commun. 2009, 10: 1207-1211. 10.1016/j.catcom.2009.01.030. Ranu BC, Saha A, Jana R: Microwave-Assisted Simple and Efficient Ligand Free Copper Nanoparticle Catalyzed Aryl-Sulfur Bond Formation. Adv Synth Catal. 2007, 349: 2690-2696. 10.1002/adsc.200700289. Bhadra S, Saha A, Ranu BC: One-pot copper nanoparticle-catalyzed synthesis of S-aryl- and S-vinyl dithiocarbamates in water: high diastereoselectivity achieved for vinyl dithiocarbamates. Green Chem. 2008, 10: 1224-1230. 10.1039/b809200a. Kidwai M, Bansal V, Saxena A, Aerry S, Mozumdar S: Cu-Nanoparticles: efficient catalysts for the oxidative cyclization of Schiffs’ bases. Tetrahedron Lett. 2006, 47: 8049-8053. 10.1016/j.tetlet.2006.09.066. Singh P, Katyal A, Kalra R, Chandra R: Copper nanoparticles in an ionic liquid: an efficient catalyst for the synthesis of bis-(4-hydroxy-2-oxothiazolyl)methanes. Tetrahedron Lett. 2008, 49: 727-730. 10.1016/j.tetlet.2007.11.106. Ahammed S, Saha A, Ranu BC: Hydrogenation of Azides over Copper Nanoparticle Surface Using Ammonium Formate in Water. J Org Chem. 2011, 76: 7235-7239. 10.1021/jo200915h. Saha A, Ranu BC: Highly Chemoselective Reduction of Aromatic Nitro Compounds by Copper Nanoparticles/Ammonium Formate. J Org Chem. 2008, 73: 6867-6870. 10.1021/jo800863m. Peng YQ, Song GH: Simultaneous microwave and ultrasound irradiation: A rapid synthesis of hydrazides. Green Chem. 2001, 3: 302-304. 10.1039/b108878p. Peng YQ, Dou RL, Song GH: Surface cleaning under combined microwave and ultrasound irradiation: flash synthesis of 4H-pyrano[2,3-c]pyrazoles in aqueous media. Green Chem. 2006, 8: 573-575. 10.1039/b601209d. Feng HD, Li Y, Van der Eycken EV, Peng YQ, Song GH: Synthesis of polysubstituted pyridines under combined microwave and ultrasound irradiation: K2CO3-promoted tandem addition/cyclization/hydrogen shift process. Tetrahedron Lett. 2012, 53: 1160-1162. 10.1016/j.tetlet.2011.12.103. Feng HD, Lin SJ, Wang JY, Song GH, Peng YQ: Aqueous heterogeneous synthesis of polysubstituted 2,6-dicyanoanilines via combined microwave and ultrasound-assisted multicomponent reaction. Green Process Synth. 2012, 1: 463-468. Feng HD, Ying XL, Peng YQ, Van der Eycken EV, Liu CD, Zhao SS, Song GH: FeCl3- promoted synthesis of 1, 3, 4-thiadiazoles under combined microwave and ultrasound irradiation in water. Monatsh Chem. 2013, 144: 681-686. 10.1007/s00706-012-0846-x. Zhu HT, Zhang CY, Yin YS: Novel synthesis of copper nanoparticles: influence of the synthesis conditions on the particle size. Nanotechnology. 2005, 16: 3079-3083. 10.1088/0957-4484/16/12/059. Zhu HT, Zhang CY, Yin YS: Rapid synthesis of copper nanoparticles by sodium hypophosphite reduction in ethylene glycol under microwave irradiation. J Crystal Growth. 2004, 270: 722-728. 10.1016/j.jcrysgro.2004.07.008. Park BK, Jeong S, Kim D, Moon J, Lim S, Kim JS: Synthesis and size control of monodisperse copper nanoparticles by polyol method. J Colloid Interface Sci. 2007, 311: 417-424. 10.1016/j.jcis.2007.03.039. Jin ZH, Wang XY, Wang ST, Li D, Lu GZ: The effect of triethylamine on the hydrodechlorination of chlorophenols on Pd/C at low temperature. Catal Commun. 2009, 10: 2027-2030. 10.1016/j.catcom.2009.07.024. Corma A, Concepcin P, Serna P: A different reaction pathway for the reduction of aromatic nitro compounds on gold catalysts. Angew Chem Int Ed. 2007, 46: 7266-7269. 10.1002/anie.200700823.