铁催化硼烷氢转移还原芳香硝基化合物
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摘要
发展了一种以硫酸铁为催化剂,硼烷四氢呋喃为氢源,在温和条件下实现了铁催化硼烷氢转移高效还原芳香硝基化合物的方法,合成了17个芳香胺衍生物,产率68%～90%,其结构经~1H NMR和~(13)C NMR确证。
A general and efficient method for Fe-catalyzed transfer hydrogenation of aromatic nitro compounds with borane under mild reaction conditions was developed, using ferric sulfate as catalyst and borane tetrahydrofuran as hydrogen source. Seventeen aromatic amine derivatives were synthesized in 68%～90% yields. The structures were confirmed by ~1H NMR and ~(13)C NMR.
A general and efficient method for Fe-catalyzed transfer hydrogenation of aromatic nitro compounds with borane under mild reaction conditions was developed, using ferric sulfate as catalyst and borane tetrahydrofuran as hydrogen source. Seventeen aromatic amine derivatives were synthesized in 68%～90% yields. The structures were confirmed by ~1H NMR and ~(13)C NMR.
引文
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[3] WIENH?FER G,SORRIBES I,BODDIEN A,et al.General and selective iron-catalyzed transfer hydrogenation of nitroarenes without base[J].J Am Chem Soc,2011,133(32):12875-12879.
[4] CAMPOS C H,ROSENBERG E,FIERRO J L G,et al.Hydrogenation of nitro-compounds over rhodium catalysts supported on poly[acrylic acid]/Al2O3 composites[J].Applied Catalysis A:General,2015,489(489):280-291.
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[6] LIU X,LI H Q,YE S,et al.Gold-catalyzed direct hydrogenative coupling of nitroarenes to synthesize aromatic azo compounds[J].Angew Chem Int Ed,2014,53(29):7624-7628.
[7] SHI X,WANG X,SHANG X,et al.High performance and active sites of a ceria-supported palladium catalyst for solvent-free chemoselective hydrogenation of nitroarenes[J].Chem Cat Chem,2017,9(19):3743-3751.
[8] LI W,ARTZ J,BROICHER C,et al.Superior activity and selectivity of heterogenized cobalt catalysts for hydrogenation of nitroarenes[J].Catal Sci Technol,2019,9(1):157-162.
[9] WANG D,ASTRUC D.The golden age of transfer hydrogenation[J].Chem Rev,2015,115(13):6621-6686.
[10] DEY R,MUKHERJEE N,AHAMMED S,et al.Highly selective reduction of nitroarenes by iron(0) nanoparticles in water[J].Chem Commun,2012,48(64):7982-7984.
[11] G?KSU H,HO S F,METIN ?,et al.Tandem dehydrogenation of ammonia borane and hydrogenation of nitro/nitrile compounds catalyzed by graphene-supported NiPd alloy nanoparticles [J].ACS Catal,2014,4(6):1777-1782.
[12] PORWAL D,OESTREICH M.B(C6F5)3-catalyzed reduction of aromatic and aliphatic nitro groups with hydrosilanes[J].2016,2016(20):3307-3309.
[13] METIN ?,MENDOZA-GARCIA A,DALMIZRAK D,et al.FePd alloy nanoparticles assembled on reduced graphene oxide as a catalyst for selective transfer hydrogenation of nitroarenes to anilines using ammonia borane as a hydrogen source[J].Catal Sci Technol,2016,6(15):6137-6143.
[14] SHEN M,LIU H,YU C,et al.Room-temperature chemoselective reduction of 3-nitrostyrene to 3-vinylaniline by ammonia borane over Cu nanoparticles[J].J Am Chem Soc,2018,140(48):16460-16463.
[15] DALICSEK Z,POLLREISZ F,G?M?RY á,et al.Recoverable fluorous CBS methodology for asymmetric reduction of ketones[J].Org Lett,2005,7(15):3243-3246.
[16] COREY E J,HELAL C J.Reduction of carbonyl compounds with chiral oxazaborolidine catalysts:A new paradigm for enantioselective catalysis and a powerful new synthetic method[J].Angew Chem Int Ed,1998,37(15):1986-2012.
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[18] SORRIBES I,LIU L,CORMA A.Nanolayered Co-Mo-S catalysts for the chemoselective hydrogenation of nitroarenes[J].ACS Catal,2017,7(4):2698-2708.
[19] SHEE S,PAUL B,KUNDU S.Counter anion controlled reactivity switch in transfer hydrogenation:A case study between ketones and nitroarenes[J].Chemistry Select,2017,2(4):1705-1710.
[20] RACYS D T,SHARIF S A I,PIMLOTT S L,et al.Silver(I)-catalyzed iodination of arenes:Tuning the Lewis acidity of N-Iodosuccinimide activation[J].J Org Chem,2016,81(3):772-780.
[21] GEVORGYAN A,MKRTCHYAN S,GRIGORYAN T,et al.Application of silicon-initiated water splitting for the reduction of organic substrates[J].Chem Plus Chem,2018,83(5):375-382.
[22] GARCíA N,GARCíA-GARCíA P,FERNáNDEZ-RODRíGUEZ M A,et al.Pinacol as a new green reducing agent:Molybdenum-catalyzed chemoselective reduction of sulfoxides and nitroaromatics[J].Adv Synth Catal,2012,354(2-3):321-327.
[23] KOMáROMI A,SZABó F,NOVáK Z.Activity of palladium on charcoal catalysts in cross-coupling reactions[J].Tetrahedron Lett,2010,51(41):5411-5414.