Facile Reduction of Nitroarenes into Anilines and Nitroalkanes into Hydroxylamines via the Rapid Activation of Ammonia⋅ Borane Complex by Supported Gold Nanoparticles
作者： Eleni Vasilikogiannaki , Charis Gryparis , Vasiliki Kotzabasaki , Ioannis N. Lykakis , Manolis Stratakis
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摘要: Gold nanoparticles supported on titania catalyse, even at a ppm loading level, the quantita- tive reduction of nitroarenes into anilines and nitro- alkanes alkylhydroxylamines by ammonia· borane complex. No dehalohalogenation was seen in case chloro- or bromonitroarenes, while ester, cyano, carboxylic acid functionalities also remain intact. The nitroarene to aniline pathway does not require nitrosoarenes as inter- mediate products.
sci-hub.se 参考文章(66)
George G. Wu, Frank X. Chen, Danny LaFrance, Zhijian Liu, Scott G. Greene, Yee-Shing Wong, Ji Xie, A novel iodide-catalyzed reduction of nitroarenes and aryl ketones with H3PO2 or H3PO3: its application to the synthesis of a potential anticancer agent. Organic Letters. ,vol. 13, pp. 5220- 5223 ,(2011) , 10.1021/OL102174W
Gerrit Wienhöfer, Iván Sorribes, Albert Boddien, Felix Westerhaus, Kathrin Junge, Henrik Junge, Rosa Llusar, Matthias Beller, General and Selective Iron-Catalyzed Transfer Hydrogenation of Nitroarenes without Base Journal of the American Chemical Society. ,vol. 133, pp. 12875- 12879 ,(2011) , 10.1021/JA2061038
Juan Su, Xiao-Xin Zou, Guo-Dong Li, Lu Li, Jun Zhao, Jie-Sheng Chen, Porous vanadium-doped titania with active hydrogen: a renewable reductant for chemoselective hydrogenation of nitroarenes under ambient conditions. Chemical Communications. ,vol. 48, pp. 9032- 9034 ,(2012) , 10.1039/C2CC33969B
Androniki Psyllaki, Ioannis N. Lykakis, Manolis Stratakis, Reaction of hydrosilanes with alkynes catalyzed by gold nanoparticles supported on TiO2 Tetrahedron. ,vol. 68, pp. 8724- 8731 ,(2012) , 10.1016/J.TET.2012.08.021
Seyoung Kim, Eunsuk Kim, B. Moon Kim, Fe3O4 nanoparticles: a conveniently reusable catalyst for the reduction of nitroarenes using hydrazine hydrate. Chemistry-an Asian Journal. ,vol. 6, pp. 1921- 1925 ,(2011) , 10.1002/ASIA.201100311
Matthew E. Sloan, Anne Staubitz, Kajin Lee, Ian Manners, Scope and Selectivity of Heterogeneous Rh0-Catalyzed Tandem Dehydrocoupling/Hydrogenation Using Me2NH·BH3 as a Stoichiometric H2 Source European Journal of Organic Chemistry. ,vol. 2011, pp. 672- 675 ,(2011) , 10.1002/EJOC.201001332
Jun-Min Yan, Xin-Bo Zhang, Tomoki Akita, Masatake Haruta, Qiang Xu, One-Step Seeding Growth of Magnetically Recyclable Au@Co Core−Shell Nanoparticles: Highly Efficient Catalyst for Hydrolytic Dehydrogenation of Ammonia Borane Journal of the American Chemical Society. ,vol. 132, pp. 5326- 5327 ,(2010) , 10.1021/JA910513H
Ivan Pogorelić, Mirela Filipan-Litvić, Sonja Merkaš, Goranka Ljubić, Ivica Cepanec, Mladen Litvić, Rapid, efficient and selective reduction of aromatic nitro compounds with sodium borohydride and Raney nickel Journal of Molecular Catalysis A-chemical. ,vol. 274, pp. 202- 207 ,(2007) , 10.1016/J.MOLCATA.2007.05.020
Avelino Corma, Hermenegildo Garcia, Supported gold nanoparticles as catalysts for organic reactions Chemical Society Reviews. ,vol. 37, pp. 2096- 2126 ,(2008) , 10.1039/B707314N
Michel Couturier, John L Tucker, Brian M Andresen, Pascal Dubé, Steven J Brenek, Joanna T Negri, Palladium catalyzed activation of borane–amine adducts: rate enhancement of amine–borane methanolysis in the reduction of nitrobenzenes to anilines Tetrahedron Letters. ,vol. 42, pp. 2285- 2288 ,(2001) , 10.1016/S0040-4039(01)00166-6