Research progress of metal complex catalysts with ionic substituents on ligand

doi:10.3969/j.issn.0438-1157.2013.01.022

Abstract

Abstract: Conventional organic substituents on the ligand of metal complex catalysts have been widely used to tune their activities and selectivities.Recently, ionic substituents, which usually enable the homogeneous catalyst dissolve in water and be recovered, are also involved in improving the activity of catalyst.The research progress of how ionic substituents on the ligand of metal complex catalyst tuned its activity in the past decade is reviewed.Furthermore, the problems, challenges, and directions of this field are presented.

Key words: ionic substituent, metal complex, catalyst

摘要： 常规有机取代基在调节催化剂活性方面已经得到广泛的应用与研究。近年来常被用于回收均相催化剂的离子取代基也逐渐被用于调节催化剂的活性。本文着重综述了近十年来离子取代基在调节金属配合物部分催化剂活性方面的研究进展,同时指出了目前离子取代基在调节催化剂催化性能方面存在的问题、挑战及发展方向。

关键词: 离子取代基, 金属配合物, 催化剂

CLC Number:

O643.36

HU Jinghui, YAO Jia, WANG Congmin, CHEN Zhirong, LI Haoran. Research progress of metal complex catalysts with ionic substituents on ligand[J]. CIESC Journal, 2013, 64(1): 198-209.

胡敬辉, 姚加, 王从敏, 陈志荣, 李浩然. 金属配合物配体上离子取代基对其部分催化性能影响的研究进展[J]. 化工学报, 2013, 64(1): 198-209.

References 102

[1]	Li Y, Yan X, Jiang G, Liu Q, Song J, Guo C. Toluene oxyfunctionalization with air over metalloporphyrins and reaction condition optimization[J].Chin.J.Chem.Eng.,2007,15(3):453-457
[2]	Yu Yingnan(宇英男),Liu Xiaoyu(刘晓瑜),Wang Libo(王力博),et al. Ethylene oligomerization catalyzed by novel iron complex /MAO[J].Chemical Industry and Engineering Progress(化工进展),2006,25(6):680-683
[3]	Wang Bing(王秉),Hu Zhiwen(胡智文),Zheng Hailing(郑海玲),Yang Hailiang(杨海亮),Huang Xiaofang(黄小芳),Zhang Dianbo(张殿波),Wan Junmin(万军民). Oxidation of catechol catalyzed by beta-cyclodextrin-Cu and its reaction kinetics[J].CIESC Journal(化工学报),2009,60(6):1459-1465
[4]	Chen Hongxia(陈洪侠),Niu Lei(牛磊),Yu Yingnan(宇英男),Jiang Tao(姜涛). Investigation of propylene oligomerization catalyzed by novel post transition metal nickel complex/methylaluminoxane catalyst[J].Chemical Industry and Engineering Progress(化工进展),2008,27(11):1805-1807,1820
[5]	Ji Hongbo(纪洪波), Xu Xuexiang(许学翔),Sun Min(孙敏),Jing Zhenhua(景振华). Synthesis of β-diketones containing alkyl substituent and their titanium complexes for syndiotatic polymerization of styrene[J].Chemical Industry and Engineering Progress(化工进展),2003,22(8):850-853
[6]	Flanagan S P, Guiry P J. Substituent electronic effects in chiral ligands for asymmetric catalysis[J].J. Organomet. Chem.,2006,691(10):2125-2154
[7]	Möhring P C, Coville N J. Group 4 metallocene polymerisation catalysts:quantification of ring substituent steric effects[J].Coord.Chem.Rev.,2006,250(1):18-35
[8]	Nyokong T. Effects of substituents on the photochemical and photophysical properties of main group metal phthalocyanines[J].Coord.Chem.Rev.,2007,251(13):1707-1722
[9]	Deck P. Perfluoroaryl-substituted cyclopentadienyl complexes of transition metals[J].Coord.Chem.Rev.,2006,250(90):1032-1055
[10]	Sebesta R, Kmentova I, Toma S. Catalysts with ionic tag and their use in ionic liquids[J].Green Chem.,2008,10(5):484-496
[11]	Shaughnessy K H. Hydrophilic ligands and their application in aqueous phase metal catalyzed reactions[J].Chem. Rev.,2009,109(2):643-710
[12]	Ni B, Headley A B. Ionic-liquid-supported(ILS)catalysts for asymmetric organic synthesis[J].Chem.Eur.J.,2010,16(15):4426-4436
[13]	Huo C, Chan T H. A novel liquid phase strategy for organic synthesis using organic ions as soluble supports[J].Chem. Soc.Rev.,2010,39(8):2977-3006
[14]	Miao W, Chan T H. Ionic-liquid-supported synthesis:a novel liquid-phase strategy for organic synthesis[J].Acc.Chem.Res.,2006,39(12):897-908
[15]	Audic N, Clavier H, Mauduit M, Guillemin J C. An ionic liquid-supported ruthenium carbene complex:a robust and recyclable catalyst for ring closing olefin metathesis in ionic liquids[J].J.Am.Chem.Soc.,2003,125(31):9248-9249
[16]	Chen S, Kim J H, Ryu K Y, Lee W, Hong J, Lee S. Novel imidazolium ion tagged Ru-carbene complexes:synthesis and applications for olefin metathesis in ionic liquid[J].Tetrahedron,2009,65(17):3397-3403
[17]	Geldbach T J, Dyson P J. A versatile ruthenium precursor for biphasic catalysis and its application in ionic liquid biphasic transfer hydrogenation:conventional vs task specific catalysts[J].J.Am.Chem.Soc.,2004,126(26):8114-8115
[18]	Wakamatsu H, Saito Y, Masubuchi M, Fujita R. Synthesis of imidazolium tagged ruthenium carbene complex:remarkable activity and reusability in regard to olefin metathesis in ionic liquids[J].Synlett.,2008,110(12):1805-1808
[19]	Dai L, Li X, Yuan H, Li X, Li Z, Xu D, Fei F, Liu Y, Zhang J, Zhou Z. Ionic salt tagged ferrocenyl diphosphine imine ligands and their application to palladium catalyzed asymmetric allylic etherification[J].Tetrahedron- Asymmetry,2011,22(13):1379-1389
[20]	Geldbach T J, Laurenczy G, Scopelliti R, Dyson P J. Synthesis of imidazolium tethered ruthenium(Ⅱ)-arene complexes and their application in biphasic catalysis[J].Organometallics,2006,25(3):733-742
[21]	Cai Y Q, Lu Y, Liu Y, Gao G H. Imidazolium ionic liquid-supported diol:an efficient and recyclable phosphine-free ligand for palladium catalyzed heck reaction[J].Catal. Lett.,2007,119(1/2):154-158
[22]	Yang G, Hu X, Wu Y, Liu C, Zhang Z. Phenol oxidation catalyzed by a simple water-soluble copper catalyst with an imidazole salt tag[J].Catal.Commun.,2012,26:132-135
[23]	Thurier C, Fischmeister C, Bruneau C, Olivier H, Dixneuf P H. Ionic imidazolium containing ruthenium complexes and olefin metathesis in ionic liquids[J].J.Mol.Catal.A:Chem.,2007,268(1/2):127-133
[24]	Consorti C S, Aydos G L P, Ebeling G, Dupont J. Ionophilic phosphines:versatile ligands for ionic liquid biphasic catalysis[J].Org.Lett.,2008,10(2):237-240
[25]	Peng Y Q, Cai Y Q, Song G H, Chen J. Ionic liquid grafted Mn(Ⅲ)-Schiff base complex:a highly efficient and recyclable catalyst for the epoxidation of chalcones[J].Synlett.,2005,56(14):2147-2150
[26]	Song K, Gao H, Liu F,Pan J, Guo L, Zai S, Wu Q. Ionic liquid-supported bis-(salicylaldimine)nickel complexes:robust and recyclable catalysts for ethylene oligomerization in biphasic solvent system[J].Catal.Lett.,2009,131(3/4):566-573
[27]	Yao Q W, Zhang Y L. Olefin metathesis in the ionic liquid 1-butyl-3-methylimidazolium hexafluorophosphate using a recyclable Ru catalyst:remarkable effect of a designer ionic tag[J].Angew.Chem.Int.Ed.,2003,42(29):3395-3398
[28]	Doherty S, Goodrich P, Hardacre C, Knight J G, Nguyen M T, Parvulescu V I, Paun C. Recyclable copper catalysts based on imidazolium-tagged bis(oxazolines):a marked enhancement in rate and enantioselectivity for Diels-Alder reactions in ionic liquid[J].Adv.Synth.Catal.,2007,349(6):951-963
[29]	Doherty S, Goodrich P, Hardacre C, Parvulescu V, Paun C. Efficient heterogeneous asymmetric catalysis of the Mukaiyama aldol reaction by silica- and ionic liquid-supported Lewis acid copper(Ⅱ)complexes of bis(oxazolines)[J].Adv.Synth.Catal.,2008,350(2):295-302
[30]	Wang R, Xiao J, Twamley B, Shreeve J M. Efficient Heck reactions catalyzed by a highly recyclable palladium(Ⅱ)complex of a pyridyl-functionalized imidazolium-based ionic liquid[J].Org.Biomol.Chem.,2007,5(4):671-678
[31]	Xiao J C, Twamley B, Shreeve J M. An ionic liquid coordinated palladium complex:a highly efficient and recyclable catalyst for the Heck reaction[J].Org.Lett.,2004,6(21):3845-3847
[32]	Hu X, Mao J, Sun Y, Chen H, Li H. Acetylacetone-Fe catalyst modified by imidazole ionic compound and its application in aerobic oxidation of beta-isophorone[J].Catal.Commun.,2009,10(14):1908-1912
[33]	Dykeman R R, Yan N, Scopelliti R, Dyson P J.Enhanced rate of arene hydrogenation with imidazolium functionalized bipyridine stabilized rhodium nanoparticle catalysts[J].Inorg.Chem.,2011,50(3):717-719
[34]	Lee S G, Zhang Y J, Piao J Y, Yoon H, Song C E, Choi J H, Hong J. Catalytic asymmetric hydrogenation in a room temperature ionic liquid using chiral Rh-complex of ionic liquid grafted 1,4-bisphosphine ligand[J].Chem. Commun.,2003,48(20):2624-2625
[35]	Ding S J, Radosz M, Shen Y Q. Ionic liquid catalyst for biphasic atom transfer radical polymerization of methyl methacrylate[J].Macromolecules,2005,38(14):5921-5928
[36]	Gadenne B, Hesemann P, Moreau J J E. Easily recoverable BINOL ligand with ionic tag for asymmetric catalysis[J].Tetrahedron-Asymmetry,2005,16(11):2001-2006
[37]	Zhou Z, Li Z, Hao X, Dong X, Li X, Dai L, Liu Y, Zhang J, Huang H, Lia X, Wang J. Recyclable copper catalysts based on imidazolium-tagged C(2)-symmetric bis(oxazoline)and their application in D-A reactions in ionic liquids[J].Green Chem.,2011,13(10):2963-2971
[38]	Zhou Z, Li Z, Hao X, Zhang J, Dong X, Liu Y, Sun W, Cao D, Wang J. Catalytic effect and recyclability of imidazolium-tagged bis(oxazoline)based catalysts in asymmetric Henry reactions[J].Org.Biomol.Chem.,2012,10(10):2113-2118
[39]	Snelders D J M, Burg C, Lutz M, Spek A L, van Koten G, Gebbink R J M K. Structure-activity relationships of oligocationic, ammonium functionalized triarylphosphines as ligands in the Pd-catalyzed Suzuki-Miyaura reaction[J].Chemcatchem,2012,2(11):1425-1437
[40]	Gulajski L, Michrowska A, Bujok, R, Grela K. New tunable catalysts for olefin metathesis:controlling the initiation through electronic factors[J].J.Mol.Catal.A:Chem.,2006,254(1/2):118-123
[41]	Michrowska A, Gulajski L, Kaczmarska Z, Mennecke K, Kirschning A, Grela K. A green catalyst for green chemistry:synthesis and application of an olefin metathesis catalyst bearing a quaternary ammonium group[J].Green Chem.,2006,8(8):685-688
[42]	Gulajski L, Michrowska A, Naroznik J, Kaczmarska Z, Rupnicki L, Grela K. A highly active aqueous olefin metathesis catalyst bearing a quaternary ammonium group[J].Chemsuschem,2008,1(1/2):103-109
[43]	Zhang H, Liu Y, Lu Y, He X, Wang X, Ding X. Epoxidations catalyzed by an ionic manganese(Ⅲ)porphyrin and characterization of manganese(Ⅴ,Ⅳ)-oxo porphyrin complexes by UV-Vis spectrophotometer in ionic liquid solution[J].J.Mol.Catal.A:Chem.,2008,287(1/2):80-86
[44]	Jordan J P, Grubbs R H. Small molecule N-heterocyclic carbene containing olefin metathesis catalysts for use in water[J].Angew.Chem.Int.Ed.,2007,46(27):5152-5155
[45]	Lombardo M, Chiarucci M, Trombini C. A recyclable triethylammonium ion-tagged diphenylphosphine palladium complex for the Suzuki-Miyaura reaction in ionic liquids[J].Green Chem.,2009,11(4):574-579
[46]	Xi Z, Bazzi H S, Gladysz J A. Analogs of Grubbs’ second generation catalyst with hydrophilic phosphine ligands:phase transfer activation of ring closing alkene metathesis[J].Org.Lett.,2011,13(23):6188-6191
[47]	Wu W, Chen S, Tsai F. Recyclable and highly active cationic 2,2'-bipyridyl palladium(Ⅱ)catalyst for Suzuki cross-coupling reaction in water[J].Tetrahedron Lett.,2006,47(52):9267-9270
[48]	Wang W, Wu J, Xia C, Li F. Reusable ammonium salt-tagged NHC-Cu(Ⅰ)complexes:preparation and catalytic application in the three component click reaction[J].Green Chem.,2011,13(12):3440-3445
[49]	Snelders D J M, Kreiter R, Firet J J, van Koten G, Gebbink R J M K. Fast Suzuki-Miyaura cross-coupling reaction with hexacationic triarylphosphine Bn-Dendriphos as ligand[J].[JP2]Adv.Synth.Catal.,2008,350(2):262-266[JP]
[50]	Liu W, Wan Q, Liu Y. Oxidation of ethylbenzene(derivatives)catalyzed by a functionalized ionic liquid combined with cationic(tetrakis(N-methyl-4-pyridinium)porphyrinato)manganese(Ⅲ)and anionic phosphotungstate[J].Monatshefte Fur Chemie,2010,141(8):859-865
[51]	Liu Y, Zhang H, Lu Y, Cai Y, Liu X. Mild oxidation of styrene and its derivatives catalyzed by ionic manganese porphyrin embedded in a similar structured ionic liquid[J].Green Chem.,2007,9(10):1114-1119
[52]	Wan Q, Liu Y. The ionic palladium porphyrin as a highly efficient and recyclable catalyst for Heck reaction in ionic liquid solution under aerobic conditions[J].Catal.Lett.,2009,128(3/4):487-492
[53]	Zhang P, Wang C, Chen Z, Li H. Acetylacetone-metal catalyst modified by pyridinium salt group applied to the NHPI-catalyzed oxidation of cholesteryl acetate[J].Catal.Sci.Technol.,2011,1(7):1133-1137
[54]	Yun X, Hu X, Jin Z, Hu J, Yan C, Yao J, Li H. Copper-salen catalysts modified by ionic compounds for the oxidation of cyclohexene by oxygen[J].J.Mol.Catal.A:Chem.,2010,327(1/2):25-31
[55]	Serwicka E M, Poltowicza J, Bahranowski K T, Olejniczak Z, Jones W. Cyclohexene oxidation by Fe-, Co-, and Mn-metalloporphyrins supported on aluminated mesoporous silica[J].Appl.Catal.A.,2004,275(1/2):9-14
[56]	Rix D, Caijo F, Laurent I, Gulajski L, Grela K, Mauduit M. Highly recoverable pyridinium-tagged Hoveyda-Grubbs pre-catalyst for olefin metathesis.Design of the boomerang ligand toward the optimal compromise between activity and reusability[J].Chem.Commun.,2007,112(36):3771-3773
[57]	Rix D, Clavier H, Coutard Y, Gulajski L, Grela K, Maudint M. Activated pyridinium tagged ruthenium complexes as efficient catalysts for ring closing metathesis[J].J.Organomet.Chem.,2006,691(24/25):5397-5405
[58]	Borre E, Caijo F, Crevisy C, Mauduit M. Design of imidazolium- and pyridinium- tagged Ruthenium pre-catalysts for olefin metathesis in ionic liquids[J].Chimica Oggi-Chemistry Today,2009,27(3):20-24
[59]	Nakagaki S, Ramos A R, Benedito F L,Peralta P G, Zarbin A J G. Immobilization of iron porphyrins into porous vycor glass:characterization and study of catalytic activity[J].[JP2]J.Mol.Catal.A:Chem.,2002,185(1/2):203-210[JP]
[60]	Bahramian B, Mirkhani V, Tangestaninejad S, Moghadam M. Catalytic epoxidation of olefins and hydroxylation of alkanes with sodium periodate by water soluble manganese(Ⅲ)salen[J].J.Mol.Catal.A:Chem.,2006,244(1/2):139-145
[61]	Guerreiro P, Ratovelomanana V, Genet J P, Dellis P. Recyclable diguanidinium-BINAP and PEG-BINAP supported catalysts:syntheses and use in Rh(Ⅰ)and Ru(Ⅱ)asymmetric hydrogenation reactions[J].Tetrahedron Lett.,2001,42(20):3423-3426
[62]	Machnitzki P, Tepper M, Wenz K, Stelzer O, Herdtweck E. Water soluble phosphines(Ⅻ):Pd catalyzed P-C coupling reactions:a novel synthetic route to cationic phosphines with para- and meta- guanidiniumphenyl moieties[J].J.Organomet.Chem.,2000,602(1/2):158-169
[63]	Tenbrink G J, Arends I, Papadogianakis G, Sheldon R A. Catalytic conversions in water(Ⅹ):Aerobic oxidation of terminal olefins to methyl ketones catalysed by water soluble palladium complexes[J].Chem.Commun.,1998,112(21):2359-2360
[64]	Tenbrink G J, Arends I, Sheldon R A. Green, catalytic oxidation of alcohols in water[J].Science,2000,287(5458):1636-1639
[65]	Srinivas K A, Kumar A, Chauhan S M S. Epoxidation of alkenes with hydrogen peroxide catalyzed by iron(Ⅲ)porphyrins in ionic liquids[J].Chem.Commun.,2002,52(20):2456-2457
[66]	Jain N, Kumar A, Chauhan S M S. Metalloporphyrin and heteropoly acid catalyzed oxidation of C=NOH bonds in an ionic liquid:biomimetic models of nitric oxide synthase[J].Tetrahedron Lett.,2005,46(15):2599-2602
[67]	Choudary B M, Ramani T, Maheswaran H, Prashant L, Ranganath K V S, Kumar K V. Catalytic asymmetric epoxidation of unfunctionalised olefins using silica, LDH and resin-supported sulfonato-Mn(salen)complex[J].Adv. Synth.Catal.,2006,348(4/5):493-498
[68]	Blair D E, Diehl H. Sulfonic acid derivatives of 1,10-phenanthroline[J].Anal.Chem.,1961,33(7):867
[69]	Ma Y P, Liu H, Chen L, Cui X, Zhu J, Deng J E. Asymmetric transfer hydrogenation of prochiral ketones in aqueous media with new water-soluble chiral vicinal diamine as ligand[J].Org.Lett.,2003,5(12):2103-2106
[70]	Huang R, Shaughnessy K H. Water soluble palladacycles as precursors to highly recyclable catalysts for the Suzuki coupling of aryl bromides in aqueous solvents[J].Inorg.Chem.,2006,25(17):4105-4112
[71]	Pawar S S, Uppalla L S, Shingare M S, Thore S N. Sodium 2-(2-pyridin-3-ylethylamino)ethyl sulfonate:an efficient ligand and base for palladium-catalyzed Suzuki reaction in aqueous media[J].Tetrahedron Lett.,2008,49(41):5858-5862
[72]	Fleckenstein C, Roy S, Leuthaeusser S, Plenio H. Sulfonated N-heterocyclic carbenes for Suzuki coupling in water[J].Chem.Commun.,2007,118(27):2870-2872
[73]	Buffin B P, Clarkson J P, Belitz N L, Kundu A. Pd(Ⅱ)-biquinoline catalyzed aerobic oxidation of alcohols in water[J].J.Mol.Catal.A:Chem.,2005,225(1):111-116
[74]	Genin E, Amengual R, Michelet V, Savignac M, Jutand A, Neuville L, Genet J P. A novel water soluble m-TPPTC ligand:steric and electronic features — recent developments in Pd- and Rh-catalyzed C—C bond formations[J].Adv.Synth.Catal.,2004,346(13/14/15):1733-1741
[75]	Amengual R, Genin E, Michelet V, Savignac M, Genet J P. Convenient synthesis of new anionic water soluble phosphanes and applications in inter- and intramolecular Heck reactions[J].Adv.Synth.Catal.,2002,344(3/4):393-398
[76]	Buffin B P, Kundu A. Synthesis, characterization, and crystal structure of platinum(Ⅱ)and palladium(Ⅱ)chlorides with an acidic alpha diimine ligand[J].Inorg.Chem.Commun.,2003,6(6):680-684
[77]	Fremy G, Castanet Y, Grzybek R, Monflier E, Mortreux A, Trzeciak A M, Ziolkowski J J. A new, highly selective, water soluble rhodium catalyst for methyl acrylate hydroformylation[J].J.Organomet.Chem.,1995,505(1):11-16
[78]	Penicaud V, Maillet C, Janvier P, Pipelier M, Bujoli B. New water soluble diamine complexes as catalysts for the hydrogenation of ketones under hydrogen pressure[J].Eur.J.Org.Chem.,1999,89(7):1745-1748
[79]	Maillet C, Praveen T, Janvier P, Minguet S, Evain M, Saluzzo C, Tommasino M L, Bujoli B. Synthesis of a new water soluble C-2 symmetric chiral diamine:preliminary investigation of its catalytic properties for asymmetric hydrogenation under biphasic conditions[J].J. Org. Chem.,2002,67(23):8191-8196
[80]	Bischoff S, Kant M. Water soluble rhodium/phosphonate-phosphine catalysts for hydroformylation[J].Catal. Today,2001, 66(2/3/4):183-189
[81]	Zhang P, Gong Y, Lv Y, Guo Y,Wang Y, Wang C, Li H. Ionic liquids with metal chelate anions[J].Chem. Commun.,2012,48(17):2334-2336
[82]	Hansch C, Leo A, Taft R W. A survey of Hammett substituent constants and resonance and field parameters[J].Chem.Rev.,1991,91(2):165-195
[83]	Krygowski T M,Stepien B T. Sigma- and Pi- electron delocalization:focus on substituent effects[J].Chem. Rev.,2005,105(10):3482-3512
[84]	Raju R K, Bloom J W G, An Y, Wheeler S E. Substituent effects on non-covalent interactions with aromatic rings:[JP2]insights from computational chemistry[J].Chemphyschem,2011,[JP]12(17):3116-3130
[85]	Consorti C S, Aydos G L P, Ebeling G, Dupont J. Ionophilic phosphines:versatile ligands for ionic liquid biphasic catalysis[J].Organic Lett.,2008,10(2):237-240
[86]	Wang J, Feng H, Qin R, Fu H, Yuan M, Chen H, Li X. Asymmetric hydrogenation of aromatic ketones catalyzed by achiral monophosphine TPPTS-stabilized Ru in ionic liquids[J].[JP2]Tetrahedron-Asymmetry,2007,18(14):1643-1647[JP]
[87]	Kostas I D, Coutsolelos A G, Charalambidis G, Skondra A. The first use of porphyrins as catalysts in cross-coupling reactions:a water soluble palladium complex with a porphyrin ligand as an efficient catalyst precursor for the Suzuki-Miyaura reaction in aqueous media under aerobic conditions[J].Tetrahedron Lett.,2007,48(38):6688-6691
[88]	Michrowska A, Gulajski L, Kaczmarska Z, Mennecke K, Kirschning A,Grela K. A green catalyst for green chemistry:synthesis and application of an olefin metathesis catalyst bearing a quaternary ammonium group[J].Green Chem.,2006, 8(8):685-688
[89]	Gulajski L, Grela K. The influence of the anionic counter ion on the activity of ammonium substituted Hoveyda-Type olefin metathesis catalysts in aqueous media//Green Metathesis Chemistry:Great Challenges in Synthesis,Catalysis and Nanotechnology[M].2011:49-56
[90]	Hu X, Sun Y, Mao J, Li H. Theoretical study on the structure-reactivity relationships of acetylacetone-Fe catalyst modified by ionic compound in C—H activation reaction[J].J.Catal.,2010,272(2):320-332
[91]	Hu X, Liu C, Wu Y, Zhang Z. Structure-reactivity relationships of metalloporphyrin modified by ionic liquid and its analogue[J].J.Phys.Chem.C,2011,115(48):23913-23921
[92]	Clavier H, Audic N, Guillemin J C, Mauduit M. Olefin metathesis in room temperature ionic liquids using imidazolium tagged ruthenium complexes[J].J. Organomet. Chem.,2005,690(15):3585-3599
[93]	Penicaud V, Maillet C, Janvier P, Pipelier M, Bujoli B. New water-soluble diamine complexes as catalysts for the hydrogenation of ketones under hydrogen pressure[J].Eur.J.Org.Chem.,1999,25(7):1745-1748
[94]	Amengual R, Michelet V, Genet J P. New studies of Rh-catalyzed addition of boronic acids under basic conditions in aqueous medium[J].Tetrahedron Lett.,2002,43(34):5905-5908
[95]	Wang R H, Piekarski M M, Shreeve J M. Pyrazolyl functionalized 2-methylimidazolium-based ionic liquids and [ZK)]
[ZK(]	their palladium(Ⅱ)complexes as recyclable catalysts[J].
	Org.Biomol.Chem.,2006,4(10):1878-1886[ZK)]
[96]	Xiao J C, Shreeve J M. Synthesis of 2,2'-biimidazolium-based ionic liquids:use as a new reaction medium and ligand for palladium catalyzed Suzuki cross-coupling reactions[J].J.Org.Chem.,2005,70(8):3072-3078
[97]	Mao J, Li N, Li H, Hu X. Novel Schiff base complexes as catalysts in aerobic selective oxidation of beta-isophorone[J].J.Mol.Catal.A:Chem.,2006,258(1/2):178-184
[98]	Wang Y, Zhang J, Wang X, Antonietti M, Li H. Boron- and fluorine- containing mesoporous carbon nitride polymers:metal-free catalysts for cyclohexane oxidation[J].Angew.Chem.Int.Ed.,2010,49(19):3356-3359
[99]	Hu J, Hu Y, Mao J, Yao J, Chen Z, Li H. Cobalt Schiff base with ionic substituents on ligand as an efficient catalyst for the oxidation of 4-methyl guaiacol to vanillin[J].Green Chem.,2012,14(10):2894-2898
[100]	Hu X, Li H, Wu T. Approaching and bond breaking energies in the C—H activation and their application in catalyst design[J].J.Phys.Chem.A,2011,115(5):904-910
[101]	Sun Y, Chen K, Jia L, Li H. Toward understanding macrocycle specificity of iron on the dioxygen-binding ability:a theoretical study[J].Phys. Chem. Chem. Phys.,2011,13(30):13800-13808
[102]	Sun Y,Zhang W, Hu X, Li H. Correlation analysis of the substituent electronic effects on the allylic H-abstraction in cyclohexene by phthalimide-N-oxyl radicals:a DFT study[J].J.Phys.Chem. B,2011,114(14):4862-4869