过渡金属催化芳香偶氮化合物的合成研究进展
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摘要
芳香偶氮化合物具有独特的结构和性质,在光电材料、有机染料及有机合成等领域有着广泛的应用。开发高效合成芳香偶氮化合物的方法成为有机合成化学的研究热点之一,受到化学家们的广泛关注。近些年来,化学家们在通过过渡金属催化合成芳香偶氮化合物研究方面取得了重要进展。从芳香肼、芳香胺及芳基硝化物这3类底物出发,根据不同的过渡金属催化剂进行分类,综述芳香偶氮化合物的合成研究进展及其反应机理,就该研究领域的局限性和未来的发展前景进行了总结和展望。
Aromatic azo compounds are widely used in the fields of light electric materials,organic dyes and organic synthesis etc due to its unique structures and properties.The efficient synthesis of aromatic azo compounds has become one of the highlights in organic synthesis and aroused extensive attention of chemists.In recent years,chemists have made significant progress in the study of the catalytic synthesis of aromatic azo compounds by transition metals.In this paper,starting from aryl hydrazides,anilines and nitroaromatics,we reviewed the progress in the synthesis of aromatic azo compounds and the reaction mechanisms according to different types of transition metal catalysts.The limitations of the research are summarized and the future development is prospected.
Aromatic azo compounds are widely used in the fields of light electric materials,organic dyes and organic synthesis etc due to its unique structures and properties.The efficient synthesis of aromatic azo compounds has become one of the highlights in organic synthesis and aroused extensive attention of chemists.In recent years,chemists have made significant progress in the study of the catalytic synthesis of aromatic azo compounds by transition metals.In this paper,starting from aryl hydrazides,anilines and nitroaromatics,we reviewed the progress in the synthesis of aromatic azo compounds and the reaction mechanisms according to different types of transition metal catalysts.The limitations of the research are summarized and the future development is prospected.
引文
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[16]张鲁博,赵秀秀,庞思平,等.芳香偶氮化合物的合成研究进展[J].合成化学,2014,22(5):709-724.
[17]LIM Y K,LEE K S,CHO C G.Novel route to azobenzenes via Pd-catalyzed coupling reactions of aryl hydrazides with aryl halides,followed by direct oxidations[J].Org.Lett.,2003,5(7):979-982.
[18]EYAL D,MICHAEL G.Catalytic oxidation of hydrazo derivatives promoted by a Ti Cl3/HBr system[J].J.Am.Chem.Soc.,2007,129(45):13 784-13 785.
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[20]LU Wen-chao,XI Chan-juan.Cu Cl-catalyzed aerobic oxidative reaction of primary aromatic amines[J].Tetrahedron Lett.,2008,49(25):4 011-4 015.
[21]ZHANG Chun,JIAO Ning.Copper-catalyzed aerobic oxidative dehydrogenative coupling of anilines leading to aromatic azo compounds using dioxygen as an oxidant[J].Angew.Chem.Int.Ed.,2010,49(35):6 174-6 177.
[22]ZHU Ying-guang,SHI Yi-an.Facile Cu(Ⅰ)-catalyzed oxidative coupling of anilines to azo compounds and hydrazines with diaziridinone under mild conditions[J].Org.Lett.,2013,15(8):1 942-1 945.
[23]CAI Shuang-fei,RONG Hong-pan,YU Xiao-fei,et al.Room temperature activation of oxygen by monodispersed metal nanoparticles:oxidative dehydrogenative coupling of anilines for azobenzene syntheses[J].ACS Catal.,2013,3(4):478-486.
[24]DUTTA B,BISWAS S,SHARMA V,et al.Mesoporous manganese oxide catalyzed aerobic oxidative coupling of anilines to aromatic azo compounds[J].Angew.Chem.Int.Ed.,2016,55(6):2 171-2 175.
[25]GRIRRANE A,CORMA A,GARCIA H.Preparation of symmetric and asymmetric aromatic azo compounds from aromatic amines or nitro compounds using supported gold catalysts[J].Nat.Protoc.,2010,5(3):429-438.
[26]ZHU Huai-yong,KE Xue-bin,YANG Xu-zhuang,et al.Reduction of nitroaromatic compounds on supported gold nanoparticles by visible and ultraviolet light[J].Angew.Chem.Int.Ed.,2010,49(50):9 657-9 661.
[27]WANG Jia-qing,HU Lei,CAO Xue-qin,et al.Catalysis by Pd nanoclusters generated in situ of high-efficiency synthesis of aromatic azo compounds from nitroaromatics under H2atmosphere[J].Rsc Adv.,2013,3(15):4 899-4 902.
[28]COMBITA D,CONCEPCION P,CORMA A.Gold catalysts for the synthesis of aromatic azocompounds from nitroaromatics in one step[J].J.Catal.,2014,311:339-349.
[29]LIU Xiang,LI Hai-qian,YE Sen,et al.Gold-catalyzed direct hydrogenative coupling of nitroarenes to synthesize aromatic azo compounds[J].Angew.Chem.Int.Ed.,2014,53(29):7 624-7 628.
[30]POTHULA K,TANG Lin,ZHA Zheng-gen,et al.Bismuth nanoparticles:an efficient catalyst for reductive coupling of nitroarenes to azo-compounds[J].RSC Adv.,2015,5(101):83 144-83 148.
[31]LI Hai-qian,LIU Xiang,ZHANG Qi,et al.Deoxygenative coupling of nitroarenes for the synthesis of aromatic azo compounds with CO using supported gold catalysts[J].Chem.Commun.,2015,51(56):11 217-11 220.
[32]ZHANG Yu-feng,MOHAMED M.Convenient electrocatalytic synthesis of azobenzenes from nitroaromatic derivatives using Sm I2[J].ACS Catal.,2017,7(12):8 480-8 486.
[2]DRUMMOND C J,GRIESER F,HEALY T W.Acid-base equilibria in aqueous micellar solutions.Part 4.Azo indicators[J].J.Chem.Soc.,Faraday Trans.,1989,85(3):561-578.
[3]IKEDA T,TSUTUMI O.Optical switching and image storage by means of azobenzene liquid-crystal films[J].Science,1995,268(5 219):1 873-1 875.
[4]BANDARAB H M D,BURDETTE S C.Photoisomerization in different classes of azobenzene[J].Chem.Soc.Rev.,2012,41(5):1 809-1 825.
[5]HUYNH M H V,HISKEY M A,HARTLINE E L,et al.Polyazido high-nitrogen compounds:hydrazo and azo-1,3,5-triazine[J].Angew.Chem.Int.Ed.,2004,43(37):4 924-4 928.
[6]QI Cai,LI Sheng-hua,LI Yu-chuan,et al.Synthesis and promising properties of a new family of high-nitrogen compounds:polyazido-and polyamino-substituted N,N'-azo-1,2,4-triazoles[J].Chem.Eur.J.,2012,18(51):16 562-16 570.
[7]NAUD D L,HISKEY M A,HARRY H H.Synthesis and explosive properties of 5,5'-dinitro-3,3'-azo-1H-1,2,4-triazole(DNAT)[J].J.Energ.Mater.,2003,21(1):57-62.
[8]黄房生,陈训,谢应,等.过渡金属催化偶氮基导向的C(sp2)-H键官能团化研究进展[J].有机化学,2017,37(1):31-39.
[9]NGUYEN L T H,GIGANT N,JOSEPH D.Advances in direct metal-catalyzed functionalization of azobenzenes[J].ACS Catal.,2018,8(2):1 546-1 579.
[10]MART R J,ALLEMANN R K.Azobenzene photocontrol of peptides and proteins[J].Chem.Commun.,2016,52(83):12 262-12 277.
[11]BROICHHAGEN J,FRANK J A,TRAUNER D.A roadmap to success in photopharmacology[J].Acc.Chem.Res.,2015,48(7):1 947-1 960.
[12]BEHARRY A A,WOOLLEY G A.Azobenzene photoswitches for biomolecules[J].Chem.Soc.Rev.,2011,40(8):4422-4437.
[13]MRMUT O,BARRETT C J.Using light to control physicalproperties of polymers and surfaces with azobenzene chromophores[J].Pure Appl.Chem.,2004,76(7/8):1 445-1 465.
[14]BAFANA A,DEVI S S,CHAKRABARTI T.Azo dyes:past,present and the future[J].Environ.Rev.,2011,19:350-371.
[15]钦传光,李洋,李海亮,等.芳香偶氮衍生物合成策略研究的新进展[J].有机化学,2013,33(3):444-457.
[16]张鲁博,赵秀秀,庞思平,等.芳香偶氮化合物的合成研究进展[J].合成化学,2014,22(5):709-724.
[17]LIM Y K,LEE K S,CHO C G.Novel route to azobenzenes via Pd-catalyzed coupling reactions of aryl hydrazides with aryl halides,followed by direct oxidations[J].Org.Lett.,2003,5(7):979-982.
[18]EYAL D,MICHAEL G.Catalytic oxidation of hydrazo derivatives promoted by a Ti Cl3/HBr system[J].J.Am.Chem.Soc.,2007,129(45):13 784-13 785.
[19]ABDESSAMAD G,AVELINO C,HERMENEGILDO G.Gold-catalyzed synthesis of aromatic azo compounds from anilines and nitroaromatics[J].Science,2008,322(5 908):1 661-1 664.
[20]LU Wen-chao,XI Chan-juan.Cu Cl-catalyzed aerobic oxidative reaction of primary aromatic amines[J].Tetrahedron Lett.,2008,49(25):4 011-4 015.
[21]ZHANG Chun,JIAO Ning.Copper-catalyzed aerobic oxidative dehydrogenative coupling of anilines leading to aromatic azo compounds using dioxygen as an oxidant[J].Angew.Chem.Int.Ed.,2010,49(35):6 174-6 177.
[22]ZHU Ying-guang,SHI Yi-an.Facile Cu(Ⅰ)-catalyzed oxidative coupling of anilines to azo compounds and hydrazines with diaziridinone under mild conditions[J].Org.Lett.,2013,15(8):1 942-1 945.
[23]CAI Shuang-fei,RONG Hong-pan,YU Xiao-fei,et al.Room temperature activation of oxygen by monodispersed metal nanoparticles:oxidative dehydrogenative coupling of anilines for azobenzene syntheses[J].ACS Catal.,2013,3(4):478-486.
[24]DUTTA B,BISWAS S,SHARMA V,et al.Mesoporous manganese oxide catalyzed aerobic oxidative coupling of anilines to aromatic azo compounds[J].Angew.Chem.Int.Ed.,2016,55(6):2 171-2 175.
[25]GRIRRANE A,CORMA A,GARCIA H.Preparation of symmetric and asymmetric aromatic azo compounds from aromatic amines or nitro compounds using supported gold catalysts[J].Nat.Protoc.,2010,5(3):429-438.
[26]ZHU Huai-yong,KE Xue-bin,YANG Xu-zhuang,et al.Reduction of nitroaromatic compounds on supported gold nanoparticles by visible and ultraviolet light[J].Angew.Chem.Int.Ed.,2010,49(50):9 657-9 661.
[27]WANG Jia-qing,HU Lei,CAO Xue-qin,et al.Catalysis by Pd nanoclusters generated in situ of high-efficiency synthesis of aromatic azo compounds from nitroaromatics under H2atmosphere[J].Rsc Adv.,2013,3(15):4 899-4 902.
[28]COMBITA D,CONCEPCION P,CORMA A.Gold catalysts for the synthesis of aromatic azocompounds from nitroaromatics in one step[J].J.Catal.,2014,311:339-349.
[29]LIU Xiang,LI Hai-qian,YE Sen,et al.Gold-catalyzed direct hydrogenative coupling of nitroarenes to synthesize aromatic azo compounds[J].Angew.Chem.Int.Ed.,2014,53(29):7 624-7 628.
[30]POTHULA K,TANG Lin,ZHA Zheng-gen,et al.Bismuth nanoparticles:an efficient catalyst for reductive coupling of nitroarenes to azo-compounds[J].RSC Adv.,2015,5(101):83 144-83 148.
[31]LI Hai-qian,LIU Xiang,ZHANG Qi,et al.Deoxygenative coupling of nitroarenes for the synthesis of aromatic azo compounds with CO using supported gold catalysts[J].Chem.Commun.,2015,51(56):11 217-11 220.
[32]ZHANG Yu-feng,MOHAMED M.Convenient electrocatalytic synthesis of azobenzenes from nitroaromatic derivatives using Sm I2[J].ACS Catal.,2017,7(12):8 480-8 486.