手性salen化合物是近几年发展起来的用于不对称催化反应的高效催化剂,自合成以来一直受到人们的关注。目前均相手性salen研究已相对成熟,但距离实现进一步的工业化还有很大差距。手性 salen化合物的固载化可望实现手性salen的工业化应用,已成为本领域的研究热点。从无机载体、有机载体和近几年发展起来的有机-无机复合载体3个方面综述了固载手性salen化合物的不同方法及研究进展,并做了分析比较。
Since chiral salen compounds were synthesized,they developed rapidly.Chiral salen compounds were widely used as catalysis for asymmetric reactions,but it was difficult to achieve industrial production.The im-mobilization of chiral salen compounds was found to be more effective to be applied to industrial production,and it attracted more and more attention.This review summarized different strategies and development to immobi-lize chiral salen compounds,going from organic supports,inorganic supports and new types of organic-inorganic hybrid material supports.The analysis and comparison of supported chiral salen compounds were also presented.
参考文献
[1] | Paul McMorn;Graham J.Hutchings .Heterogeneous enantioselective catalysts: strategies for the immobilisation of homogeneous catalysts[J].Chemical Society Reviews,2004(2):108-122. |
[2] | Darensbourg DJ.;Yarbrough JC. .Mechanistic aspects of the copolymerization reaction of carbon dioxide and epoxides, using a chiral salen chromium chloride catalyst[J].Journal of the American Chemical Society,2002(22):6335-6342. |
[3] | Corma A .Preparation and catalytic properties of new meso-porous materials[J].Topics in Catalysis,1997,4(3-4):249-260. |
[4] | Sabater M J;Corma A;Domenech A et al.Chiral salen manganese complex encapsulated within zeolite Y:aheter-ogeneous enantioselective catalyst for the epoxidation ofalkenes[J].Chemistry Communications,1997,33(100):1285-1286. |
[5] | Ogunwumi S B;Bein T .Intrazeolite assembly of a chiral manganese salen epoxidation catalyst[J].Chem Com-mun,1997,33(09):901-902. |
[6] | Kahlen W;Wagner H H;Holderich W E .Asymmetric catalysis on solids[J].Catalysis Letters,1998,54:85-96. |
[7] | Gigante B.;Garcia H.;Sabater MJ.;Corma A. .Assessment of the negative factors responsible for the decrease in the enantioselectivity for the ring opening of epoxides catalyzed by chiral supported Cr(III)-salen complexes[J].Catalysis Letters,2000(1/2):113-119. |
[8] | Schuster Carmen .Modification of faujasites to generate novel hosts for "ship-in-a-bottle" complexes[J].Catalysis Today,2000(3/4):193-207. |
[9] | Schuster C;Mollmann E;Tompos A et al.Highly ste-reoselective epoxidation of(-)-α-pinene over chiral tran-sition metal(salen)complexes occluded in zeolitic hosts[J].Catalysis Letters,2001,74:69-75. |
[10] | Groen, JC;Moulijn, JA;Perez-Ramirez, J .Decoupling mesoporosity formation and acidity modification in ZSM-5 zeolites by sequential desilication-dealumination[J].Microporous and Mesoporous Materials,2005(2):153-161. |
[11] | Kumar S.;Hegde SG.;Sivasanker S.;Sinha AK. .Influence of mild dealumination on physicochemical, acidic and catalytic properties of H-ZSM-5[J].Journal of molecular catalysis, A. Chemical,2000(1/2):115-120. |
[12] | Frunza L;Kosslick H;Landmesser H et al.Heteroge-neous catalysis:enigmas,illusions,challenges,real-ities,and emergent strategies of design[J].Journal of Molecular Catalysis A:Chemical,1997,128(18):123-179. |
[13] | Kureshy R I;Khan N H;Abdi S H R et al.Dicationic chiral Mn(Ⅲ)salen complex exchanged in the interlay-ers of montmorillonite clay:A heterogeneous enantiose-lective catalysts for epoxidation of nonfunctionalised al-kenes[J].Catalysis Letters,2004,221(01):234-240. |
[14] | Kureshy R I;Khan N H;Abdi S H R et al.Immobi-lization of dicationic Mn(Ⅲ)salen in the interlayers of montmorillonite clay for enantioselective epoxidation of non-functionalised alkenes[J].Catalysis Letters,2003,91(3-4):207-210. |
[15] | Bhattacharjee S;Anderson J A .Synthesis and character-ization of novel chiral sulfonato-salen-manganese(Ⅲ)complex in a zinc-aluminium LDH host[J].Chem Com-mun,2004,40(05):554-555. |
[16] | 楼兰兰,董铭铭,彭晓杰,于凯,刘双喜.固定化离子液体固载手性salen Mn(Ⅲ)催化剂的制备及其在烯烃环氧化反应中的应用[J].南开大学学报(自然科学版),2007(03):62-66. |
[17] | Baleizao C;Gigante B;Corma A et al.On the activity of chiral chromium salen complexes covalently bound to solid silicates for the enantioselective epoxide ring open-ing[J].Applied Catalysis A:General,2002,228:279-288. |
[18] | 郑欣梅,齐彦兴,张小明,索继栓.新型分子筛SBA-15固载手性Salen Mn(Ⅲ)配合物的合成及其催化性能的研究[J].分子催化,2003(06):461-464. |
[19] | Xiaochuan Zou;Xiangkai Fu;Yuedong Li .Highly Enantioselective Epoxidation of Unfunctionalized Olefins Catalyzed by Chiral Jacobsen's Catalyst Immobilized on Phenoxy-Modified Zirconium Poly(syrene-phenylvinylphos-phonate)phosphate[J].Advanced synthesis & catalysis,2010(1):163-170. |
[20] | Zhang HD;Xiang S;Li C .Enantioselective epoxidation of unfunctionalised olefins catalyzed by Mn(salen) complexes immobilized in porous materials via phenyl sulfonic group[J].Chemical communications,2005(9):1209-1211. |
[21] | Zhang H;Zhang Y;Li C J .Heterogeneous catalysis:enigmas,illusions,challenges,realities,and emergent strategies of design[J].CHEMICAL PHYSICS LETTERS,2008,128:369-371. |
[22] | Kim GJ.;Shin JH. .The catalytic activity of new chiral salen complexes immobilized on MCM-41 by multi-step grafting in the asymmetric epoxidation[J].Tetrahedron letters: The International Journal for the Rapid Publication of Preliminary Communications in Organic Chemistry,1999(37):6827-6830. |
[23] | Kim GJ.;Shin JH. .The synthesis of new chiral salen complexes immobilized on MCM-41 by grafting and their catalytic activity in the asymmetric borohydride reduction of ketones[J].Catalysis Letters,1999(3/4):205-212. |
[24] | Kim J H;Kim G J .Enantioselectivities of chiral Ti(Ⅳ)salen complexes immobilizedon MCM-41in asymmetric trimethylsilylcyanation of benzaldehyde[J].Catalysis Letters,2004,92(3-4):123-130. |
[25] | 赵继全,张雅然,张月成.MCM-41负载手性Salen-Mn(Ⅲ)配合物的制备及其对不对称环氧化的催化性能[J].催化学报,2007(01):85-90. |
[26] | Minutulo F;Antonella P .Heterogeneous asymmetic ep-oxidation of unfuctionalized olefins catalyzed by poly-mer-bound(salen)managanese complexes[J].Tetrah Edron:Asymmetry,1996,7:2293-2302. |
[27] | Song C E;Roh E J;Yu B M et al.Heterogeneous asymmetric epoxidation of alkenes catalysed by a poly-mer-bound(pyrrolidine salen)manganese(Ⅲ)complex[J].Chemistry Communications,2000,7:615-616. |
[28] | 郭锋,赵继全,张月成,冯磊.聚苯乙烯负载手性 Salen-Mn(Ⅲ)配合物的制备及其对不对称环氧化反应的催化性能[J].功能高分子学报,2008(01):30-35,49. |
[29] | 徐国津,魏赛丽,樊颖果,朱丽波,唐玉海,郑元锁.聚甲基丙烯酸羟乙酯负载手性 Mn(III)salen 配合物催化α-甲基苯乙烯的不对称环氧化反应[J].催化学报,2012(03):473-477. |
[30] | Carlos Baleizao;Barbara Gigante;Debasish Das;Mercedes Alvaro;Hermenegildo Garcia;Avelino Corma .Synthesis and catalytic activity of a chiral periodic mesoporous organosilica (ChiMO)[J].Chemical communications,2003(15):1860-1861. |
[31] | Carlos Baleizao;Barbara Gigante;Debasish Das;Mercedes Alvaro;Hermenegildo Garcia;Avelino Corma .Periodic mesoporous organosilica incorporating a catalytically active vanadyl Schiff base complex in the framework[J].Journal of Catalysis,2004(1):106-113. |
[32] | Gang W;Xiangkai F;Ma Xuebin et al.Syntheses and electrochromic and fluorescence properties of three double dithienylpyrroles derivatives[J].Electrochimica Acta,2011,56(18):6352-6360. |
[33] | Wu, C.;Fu, X.;Li, S. .A highly efficient, large-scale, asymmetric direct aldol reaction employing simple threonine derivatives as recoverable organocatalysts in the presence of water[J].European journal of organic chemistry,2011(7):1291-1299. |
[34] | Tu X B;Fu X K;Yan S et al.Chiral Salen Mn(Ⅲ)im-mobolized on sulfoalkyl modified ZSP-IPPA as an effective catalyst for asymmetric epoxidation of unfunctionalized ol-fins[J].Inorganic Chemistry Communications,2010,13:404-407. |
[35] | Bai R F;Fu X K;Ma X B et al.Chiral Salen Mn(Ⅲ)complex axial coordination immobilized on diamine mod-ified ZSPP and their catalytic epoxidation of styrene[J].CATALYSIS COMMUNICATIONS,2008,9:1588-1594. |
[36] | Zou X C;Fu X K;Li Y D et al.Higllly enalltioselective epoxidation of unfunctionalized olefins catalyzed by chiral jacobsens catalyst immobilized on phenoxy-modi-fied zirconium poly(syrenephenylvinylphosphonate)phosphate[J].Synth Catal,2010,352:163-170. |
[37] | Ren W S;Fu X K .Chiral Mn(Ⅲ)salen complexes cova-lently boned on zirconium oligostyrenylphosphonate-phosphates as catalysts for enantioselective epoxidation of nonfunctionalized alkenes[J].Molecular Catalysis A:Chemical,2009,312:40-47. |
[38] | Ren W S;Fu X K;Ding P P et al.Enaltioselective ep-oxidation of unfunctionalized olefins catalyzed by chiral salen Mn(Ⅲ)catalyst immobilized on zirconium obligo-styrenylphonate-phosphate[J].CATALYSIS COMMUNICATIONS,2009,10:788-793. |
- 下载量()
- 访问量()
- 您的评分:
-
10%
-
20%
-
30%
-
40%
-
50%