硒催化硼氢化钠还原芳香族硝基化合物制备芳胺
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摘要
以硒粉为催化剂、硼氢化钠为还原剂在温和条件下还原芳香族硝基化合物制备芳胺。以10mmol硝基苯为底物考察了溶剂、反应温度、硼氢化钠及硒粉用量等对苯胺收率的影响。适宜的反应条件如下:溶剂为乙醇-水(V(乙醇)∶V(水)=3∶1),反应温度为50℃,硒粉用量为0.1g,硼氢化钠用量为12 mmol。在此条件下,10种芳香族硝基化合物被还原为相应芳胺的收率为11.2%~99.1%,底物中另一取代基的位置和性质对芳胺收率有较大影响。
Under mild conditions,aromatic nitro compounds were reduced to anilines with sodium borohydride in the presence of selenium catalyst.The influences of solvent,reaction temperature and the amount of sodium borohydride were investigated with 10 mmol nitrobenzene as substrate.The suitable reaction conditions were as follows:ethanol and water(V(ethanol)∶V(water)= 3∶1)as solvent,reaction temperature 50℃,0.1g selenium and 12 mmol sodium borohydride.Under these conditions,ten aromatic nitro compounds were reduced to corresponding anilines with 11.2% ~99.1% yields.The position and property of the other substituent of the substrate exerted great influence on the yield.
Under mild conditions,aromatic nitro compounds were reduced to anilines with sodium borohydride in the presence of selenium catalyst.The influences of solvent,reaction temperature and the amount of sodium borohydride were investigated with 10 mmol nitrobenzene as substrate.The suitable reaction conditions were as follows:ethanol and water(V(ethanol)∶V(water)= 3∶1)as solvent,reaction temperature 50℃,0.1g selenium and 12 mmol sodium borohydride.Under these conditions,ten aromatic nitro compounds were reduced to corresponding anilines with 11.2% ~99.1% yields.The position and property of the other substituent of the substrate exerted great influence on the yield.
引文
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[13]张磊,左杭冬,马鸿飞,等.硼氢化钠/碘对3,5-二硝基苯甲酸甲酯的部分还原[J].精细化工中间体,2011,41(5):29-31.
[14]张铸勇.精细有机合成单元反应[M].上海:华东理工大学出版社,2003:162-189.
[2]尹静梅,张瑞,贾颖萍,等.芳香硝基化合物还原制备芳胺的研究进展[J].化学研究,2010,21(1):96-101.
[3]JOHNSTONE R A W,Wilby A H,ENTWISTLE I D.Heterogeneous Catalytic Transfer Hydrogenation and Its Relation to Other Methods for Reduction of Organic Compounds[J].Chem Rev,1985,85(2):129-170.
[4]LAUWINER M,RYS P,WISSMANN J.Reduction of Aromatic Nitro Compounds with Hydrazine Hydrate in the Presence of an Iron Oxide Hydroxide Catalyst.I.The Reduction of Monosubstituted Nitrobenzenes with Hydrazine Hydrate in the Presence of Ferrihydrite[J].Appl Catal A:Gen,1998,172(1):141-148.
[5]蔡可迎,周颖梅,岳玮.FeO(OH)/C催化水合肼还原芳香族硝基化合物制备芳胺[J].化学世界,2009,50(7):418-420,435.
[6]PERIASAMY M,THIRUMALAIKUMAR M.Methods of Enhancement of Reactivity and Selectivity of Sodium Borohydride for Applications in Organic Synthesis[J].J Organometallic Chem,2000,609(1-2):137-151.
[7]白银娟,路军,马怀让.硼氢化钠在有机合成中的研究进展[J].应用化学,2002,19(5):409-415.
[8]POGORELI'CI,FILIPAN-LIVI'C M,MERKAS,et al.Rapid,Efficient and Selective Reduction of Aromatic Nitro Compounds with Sodium Borohydride and Raney Nickel[J].J Molec Catal A:Chem,2007,274(1-2):202-207.
[9]KIASAT A R,MIRZAJANI R,ATAEIAN F,et al.Immobilized Silver Nanoparticles on Silica Gel as an Efficient Catalyst in Nitroarene Reduction[J].Chin Chem Lett,2010,21(9):1015-1019.
[10]VADAKKEKARA R,CHAKRABORTY M,PARIKH P A.Reduction of Aromatic Nitro Compounds on Colloidal Hollow Silver Nanospheres[J].Colloids and Surfaces A:Physicochemical and Engineering Aspects,2012,399:11-17.
[11]LIU X Z,LU S W.Selective Formation of Aromatic Amines by Selenium-catalyzed Reduction of Aromatic Nitro Compounds with CO/H2O under Atmospheric Pressure[J].J Molec Catal A:Chem,2004,212(1-2):127-130.
[12]蔡可迎,马玉苗,周肖,等.硒催化水合肼还原芳香族硝基化合物制备芳胺[J].精细石油化工,2007,24(6):51-54.
[13]张磊,左杭冬,马鸿飞,等.硼氢化钠/碘对3,5-二硝基苯甲酸甲酯的部分还原[J].精细化工中间体,2011,41(5):29-31.
[14]张铸勇.精细有机合成单元反应[M].上海:华东理工大学出版社,2003:162-189.