欢迎登录材料期刊网

材料期刊网

高级检索

研究和开发环境友好的有机合成反应是"绿色化学"研究的一个重要内容,其中也包括新型绿色催化剂的研究.本文对近两年来Yb(OTf)3作为催化剂的有机合成反应按照反应类型进行了综述.进一步总结和拓展了Yb(OTf)3的催化范围,证明了稀土化合物广泛的应用前景.

参考文献

[1] Howells R D;McCown J C .Trifluoromethanesulfonic acid and derivatives[J].Chemical Reviews,1977,77(01):69.
[2] LI C J;Chan T H.Organic Reactions in Aqueous Media[M].John Wiley & Sons:New York,1997
[3] Shu Kobayashi;Masaharu Sugiura;Hidetoshi Kitagawa;William W.-L.Lam .Rare-Earth Metal Triflates in Organic Synthesis[J].Chemical Reviews,2002(6):2227-2302.
[4] Frontiers in Lanthanide Chemistry[J].Chemical Reviews,2002,102(06):2230.
[5] Mahrwald Rainer .Diastereoselection in Lewis-Acid-Mediated Aldol Additions[J].Chemical Reviews,1999(5):1095-1120.
[6] Hamada T.;Manabe K.;Ishikawa S.;Nagayama S.;Shiro M.;Kobayashi S. .Catalytic asymmetric aldol reactions in aqueous media using chiral bis-pyridino-18-crown-6-rare earth metal triflate complexes[J].Journal of the American Chemical Society,2003(10):2989-2996.
[7] Michael Arend;Bernhard Westermann;Nikolaus Risch .Modern variants of the Mannich reaction[J].Angewandte Chemie International Edition,1998(8):1044-1070.
[8] Danishiefsky S;McKee R;Schuda P F .Reactions of silyl enol ethers and lactone enolates with dimethyl (methylene) ammonium iodide. The bis-. alpha. -methylenation of pre-vemolepin and prevernomenin[J].Journal of the American Chemical Society,1976,98(21):6715.
[9] Kobayashi S.;Yasuda M.;Araki M. .ONE-POT SYNTHESIS OF BETA-AMINO ESTERS FROM ALDEHYDES USING LANTHANIDE TRIFLATE AS A CATALYST[J].Tetrahedron letters: The International Journal for the Rapid Publication of Preliminary Communications in Organic Chemistry,1995(32):5773-5776.
[10] Hattori K;Yamamoto H .Practical preparation of α-Hydroxy-βamino ester units; Stereoselective synthesis of taxot siole chain and norstatine[J].Tetrahedron,1994,50(09):2785.
[11] Adam Janczuk;Wei Zhang;Wenhua Xie;Sanzhong Lou;JinPei Cheng .Ytterbium triflate catalyzed electrophilic substitution of indoles: the synthesis of unnatural tryptophan derivatives[J].Tetrahedron letters: The International Journal for the Rapid Publication of Preliminary Communications in Organic Chemistry,2002(23):4271-4274.
[12] Riichiro Tsuji;Masamichi Yamanaka;Atsushi Nishida;Masako Nakagawa .Pictet-spengler reaction of nitrones and imines catalyzed by Yb(OTf)_3-TMSCl[J].Chemistry Letters,2002(4):428-429.
[13] Terakado M;Miyazawa M;Yamamoto K.A novel palladium (0)-catalyzed cyclization of 2,7-octadienyl carbonate containing an allylsilane moiety[J].SYNLETT,1994(02):134.
[14] Yamanaka M.;Nishida A.;Nakagawa M. .Imino ene reaction catalyzed by ytterbium(III) triflate and TMSCl or TMSOTf[J].The Journal of Organic Chemistry,2003(8):3112-3120.
[15] Deevi Basavaiah;Anumolu Jaganmohan Rao;Tummanapalli Satyanarayana .Recent advances in the baylis-hillman reaction and applications[J].Chemical Reviews,2003(3):811-891.
[16] Yang KS.;Lee WD.;Pan JF.;Chen KM. .Chiral Lewis acid-catalyzed asymmetric Baylis-Hillman reactions[J].The Journal of Organic Chemistry,2003(3):915-919.
[17] Olah G A;Krishnamurti R;Prakash G K S.In Comprehensive Organic Synthesis[M].Oxford:Pergamon Press,1991:293.
[18] Dong-Mei Cui;Masato Kawamura;Shigeru Shimada;Teruyuki Hayashi;Masato Tanaka .Synthesis of 1-tetralones by intramolecular Friedel-Crafts reaction of 4-arylbutyric acids using Lewis acid catalysts[J].Tetrahedron letters: The International Journal for the Rapid Publication of Preliminary Communications in Organic Chemistry,2003(21):4007-4010.
[19] Pravin R.Likhar;Manyam Praveen Kumar;Ananda K.Bandyopadhyay .Yb(OTf)_3 catalyzed highly regioselective allylation of aromatic epoxides: an efficient route to bishomoallyl alcohols[J].Tetrahedron letters: The International Journal for the Rapid Publication of Preliminary Communications in Organic Chemistry,2002(18):3333-3335.
[20] Hollis T K;Robinson N P;Bosnich B .Homogeneous catalysis:[Ti (Cp*)2(H2O)2]2 +: an air-stable, water-tolerant diels-alder catalyst[J].Journal of the American Chemical Society,1992,114(13):5464.
[21] Stephen Hermitage;David A. Jay;Andrew Whiting .Evidence for the non-concerted [4+2]-cycloaddition of N-aryl imines when acting as both dienophiles and dienes under Lewis acid-catalysed conditions[J].Tetrahedron letters: The International Journal for the Rapid Publication of Preliminary Communications in Organic Chemistry,2002(52):9633-9636.
[22] Kakuuchi A;Taguchi T;Hanzawa .Formation of α-amino ketones:addition of acylzirconocene chlorides to imines catalyzed by Yb (OTf)3/TMSOTf and bronsted acids and three-component reactions of acylzirconocene chlorides,aldehydes,and amines[J].European Journal of Organic Chemistry,2003,68(01):116.
[23] Curini M.;Epifano F.;Maltese F.;Rosati O. .Ytterbium triflate promoted coupling reaction between aryl alkynes and aldehydes[J].Synlett,2003(4):552-554.
[24] Vedejs E;Bennet N S;Conn L et al.Tributylphosphine-catalyzed acylations of alcohols: scope and related reactions[J].Journal of Organic Chemistry,1993,58(25):7286.
[25] Lee S;Park J H .Metallic lewis acids-catalyzed acetylation of alcohols with acetic anhydride and acetic acid in ionic liquids:study on reactivity and reusability of the catalysts[J].Journal of Molecular Catalysis A:Chemical,2003,194(1-2):49.
[26] Massimo Curini;Francesco Epifano;Federica Maltese;Ornelio Rosati .Carbamate synthesis from amines and dimethyl carbonate under ytterbium triflate catalysis[J].Tetrahedron letters: The International Journal for the Rapid Publication of Preliminary Communications in Organic Chemistry,2002(28):4895-4897.
[27] Angelo J;Maddaluno J J .Enantioselective synthesis of . beta.amino esters through high pressure-induced addition of amines to.alpha., . beta. -ethylenic esters[J].Journal of the American Chemical Society,1986,108(25):8112.
[28] Biswajit S;Debasis D;Biswadip B et al.Synthesis of βmethyl-β-alanine-l-proline-XAA tripeptides by Yb (OTf)3 catalysed Michael addition of amines to N-crotonyl-l-proline-XAA: a versatile route to cyclic β-methyl-β-alanine-derived tripeptides via ring closing metathesis[J].Tetrahedron Letters,2002,43(36):6467.
[29] Adinolfi M;Barone G;Iadonisi A et al.Efficient activation of glycosyl N-(phenyl) trifluoroacetimidate donors with ytterbium (Ⅲ)triflate in the glycosylation reaction[J].Tetrahedron Letters,2002,43(32):5573.
[30] Matteo Adinolfi;Gaspare Barone;Alfonso Iadonisi;Lorenzo Mangoni;Marialuisa Schiattarella .Activation of disarmed 2-O-alkoxycarbonylated glycosyl trichloroacetimidates with lanthanide triflates: an efficient approach for the synthesis of 1,2-trans glycosides[J].Tetrahedron letters: The International Journal for the Rapid Publication of Preliminary Communications in Organic Chemistry,2001(34):5967-5969.
[31] Matteo Adinolfi;Alfonso Iadonisi;Marialuisa Schiattarella .An approach to the highly stereocontrolled synthesis of α-glycosides. Compatible use of the very acid labile dimethoxytrityl protecting group with Yb(OTf)_3-promoted glycosidation[J].Tetrahedron letters: The International Journal for the Rapid Publication of Preliminary Communications in Organic Chemistry,2003(34):6479-6482.
[32] Mohamed Takhi;Adel A -H.Abdel Rahman;Richard R.Schmidt .Yb(OTf)_3-catalyzed C-glycosylation :highly stereoselective synthesis of C-pseudoglycals[J].Tetrahedron letters: The International Journal for the Rapid Publication of Preliminary Communications in Organic Chemistry,2001(24):4053-4056.
[33] Sharma GVM.;Kumar KR.;Sreenivas P.;Krishna PR.;Chorghade MS. .Catalytic FeCl3- or Yb(OTf)(3)-mediated synthesis of substituted tetrahydrofurans and C-aryl glycosides from 1,4-diols[J].Tetrahedron, Asymmetry: The International Journal for Repid Publication on all Aspects of Asymmetry in Orgainc, Inorganic, Organometallic, Physical and Bio-Organic Chemistry,2002(7):687-690.
[34] Yamanaka M;Nishida A;Nakagawa M .Ytterbium( Ⅲ) Triflate/TMSCl: Efficient Catalyst for Imino Ene Reaction[J].Organic Letters,2000,2(02):159.
[35] Masamichi Yamanaka;Mitsuhiro Arisawa;Atsushi Nishida;Masako Nakagawa .An intriguing effect of Yb(OTf)_3-TMSCl in the halogenation of 1,1-disubstituted alkenes by NXS: selective synthesis of allyl halides[J].Tetrahedron letters: The International Journal for the Rapid Publication of Preliminary Communications in Organic Chemistry,2002(13):2403-2406.
[36] Alessandro Dondoni;Alessandro Massi;Simona Sabbatini .Improved synthesis and preparative scale resolution of racemic monastrol[J].Tetrahedron letters: The International Journal for the Rapid Publication of Preliminary Communications in Organic Chemistry,2002(34):5913-5916.
[37] Wang LM.;Xia JJ.;Qin F.;Qian CT.;Sun J. .Yb(OTf)(3)-catalyzed one-pot synthesis of quinazolin-4(3H)-ones from anthranilic acid, amines and ortho esters (or formic acid) in solvent-free conditions[J].Synthesis: International Journal of Methods in Synthetic Organic Chemistry,2003(8):1241-1247.
[38] Serrano P.;Llebaria A.;Delgado A. .An unexpected chelation-controlled Yb(OTf)(3)-catalyzed aminolysis and azidolysis of cyclitol epoxides[J].The Journal of Organic Chemistry,2002(20):7165-7167.
[39] Rita Annunziata;Maurizio Benaglia;Laura Raimondi .Mild synthesis of enantiomerically pure imidazo-[1,2-a]azepines mediated by Yb(OTf)_3[J].Tetrahedron,2001(52):10357-10363.
[40] Habaue S.;Isobe Y.;Okamoto Y. .Stereocontrolled radical polymerization of acrylamides and methacrylamides using Lewis acids[J].Tetrahedron,2002(41):8205-8209.
[41] Suito Y;Isobe Y;Habaue S et al.Isotactic-specific radical polymerization of methacrylamides in the presence of lewis acids[J].Journal of POLYMER SCIENCE PART A:POLYMER CHEMISTRY,2002,40(14):2496.
[42] Kumareswaran R;Shahi S;Rani S.Ytterbium triflate (and trimethylsilyl triflate) catalyzed isomerization of glycidic esters to α-hydroxy-β,γ-unsaturated esters and their conversion into cyclopentanoids using Johnson-Claisen rearrangement[J].Arkivoc,2002(07):126.
[43] 戴洪兴,何洪,李佩珩,訾学红.稀土钙钛矿型氧化物催化剂的研究进展[J].中国稀土学报,2003(z2):1-15.
上一张 下一张
上一张 下一张
计量
  • 下载量()
  • 访问量()
文章评分
  • 您的评分:
  • 1
    0%
  • 2
    0%
  • 3
    0%
  • 4
    0%
  • 5
    0%