摘要
伯醇和仲醇被氧化为相应的羰基化合物是重要的官能团转换反应,目前主要通过催化的方法来实现。随着绿色化学的发展,采用环境友好的氧化剂开发新的催化氧化方法实现醇的氧化是近年来的研究热点。该文综述了2000年以来以氧气、过氧化氢以及丙酮作为氧化剂催化氧化醇研究的进展,并对不同方法的特点进行了总结,据此指出了后期绿色催化氧化醇的发展方向。
The oxidation of primary and secondary alcohols to corresponding carbonyl compounds is an important functional group conversion reaction, which is mainly achieved by catalyst. The importance of eliminating waste production and development of green process using eco-friendly oxidants to oxidize alcohols attracts much research interests. The research progress in the catalytic oxidation of alcohols using eco-friendly oxidants such as oxygen, hydrogen peroxide and acetone since 2000 is reviewed. At the same time, the characteristics of different methods are summarized. Finally, the development trend of green catalytic oxidation of alcohols is presented.
引文
[1]Mallat T,Baiker A.Oxidation of alcohols with molecular oxygen on solid catalysts[J].Chemical Reviews,2004,104(6):3037-3058.
[2]Sheldon R,Arends I,Dijksman A.New developments in catalytic alcohol oxidations for fine chemicals synthesis[J].Catalysis Today,2000,57(1/2):157-166.
[3]Shinoda S,Itagaki H,Saito Y.Dehydrogenation of methanol in the liquid phase with a homogeneous ruthenium complex catalyst[J].Journal of the Chemical Society,Chemical Communications,1985,13:860-861.
[4]Fujii T,Saito Y.Catalytic dehydrogenation of methanol with ruthenium complexes[J].Journal of Molecular Catalysis,1991,67(2):185-190.
[5]Dijksman A,Marino-González A,Payeras A,et al.Efficient and selective aerobic oxidation of alcohols into aldehydes and ketones using ruthenium/TEMPO as the catalytic system[J].Journal of the American Chemical Society,2001,123(28):6826-6833.
[6]Ji H,Yuan Q,Zhou X,et al.Highly efficient selective oxidation of alcohols to carbonyl compounds catalyzed by ruthenium(Ⅲ)meso-tetraphenylporphyrin chloride in the presence of molecular oxygen[J].Bioorganic&Medicinal Chemistry Letters,2007,17(22):6364-6368.
[7]Shapley P,Zhang N,Allen J,et al.Selective alcohol oxidation with molecular oxygen catalyzed by Os-Cr and Ru-Cr complexes[J].Journal of the American Chemical Society,2000,122(6):1079-1091.
[8]Lee M,Chang S.Highly efficient aerobic oxidation of benzylic and allylic alcohols by a simple catalyst system of[RuCl2(p-cymene)]2/Cs2CO3[J].Tetrahedron Letters,2000,41(39):7507-7510.
[9]Csjernyik G,E?ll A,Fadini A,et al.Efficient ruthenium-catalyzed aerobic oxidation of alcohols using a biomimetic coupled catalytic system[J].Journal of Organic Chemistry,2002,67(5):1657-1662.
[10]Brink G,Arends I,Sheldon R.Green,catalytic oxidation of alcohols in water[J].Science,2000,287(5458):1636-1639.
[11]Stahl S,Thorman J,Nelson R,et al.Oxygenation of nitrogencoordinated palladium(0):Synthetic,structural,and mechanistic studies and implications for aerobic oxidation catalysis[J].Journal of the American Chemical Society,2001,123(29):7188-7189.
[12]Steinhoff B,Stahl S.Ligand-modulated palladium oxidation catalysis:mechanistic insights into aerobic al cohol oxidation with the Pd(OAc)2/pyridine catalyst system[J].Organic Letters,2002,4(1):23-26.
[13]Jensen D,Pugsley J,Sigman M.Palladium-catalyzed enantioselective oxidations of alcohols using molecular oxygen[J].Journal of the American Chemical Society,2001,123(30):7475-7476.
[14]Schultz M,Park C,Sigman M.A convenient palladium-catalyzed aerobic oxidation of alcohols at room temperature[J].Chemical Communications,2002,24:3034-3035.
[15]Jensen D,Schultz M,Mueller J,et al.A well-defined complex for palladium catalyzed aerobic oxidation of alcohols:design,synthesis,and mechanistic considerations[J].Angewandte Chemie International Edition,2003,42(32):3810-3813.
[16]Asensio J,Gómez-Sal P,Andrés R,et al.Synthesis of water-soluble palladium(Ⅱ)complexes with N-heterocyclic carbene chelate ligands and their use in the aerobic oxidation of 1-phenylethanol[J].Dalton Transactions,2017,46(20):6785-6797.
[17]Liu L,Yu M,Waylandb B,et al.Aerobic oxidation of alcohols catalyzed by rhodium(Ⅲ)porphyrin complexes in water:Reactivity and mechanistic studies[J].Chemical Communications,2010,46:6353-6355.
[18]Kervinen K,Korpi H,Leskel?M,et al.Oxidation of veratryl alcohol by molecular oxygen in aqueous solution catalyzed by cobalt salen-type complexes:The effect of reaction conditions[J].Journal of Molecular Catalysis A:Chemical,2003,203(1/2):9-19.
[19]Sharma V,Jain S,Sain B.Cobalt(Ⅱ)schiff base catalyzed aerobic oxidation of secondary alcohols to ketones[J].Journal of Molecular Catalysis A:Chemical,2004,212(1/2):55-59.
[20]Muldoon J,Brown S.Practical Os/Cu-cocatalyzed air oxidation of allyl and benzyl alcohols at room temperature and atmospheric pressure[J].Organic Letters,2002,4(6):1043-1045.
[21]Kazemnejadi M,Nikookar M,Mohammadi M,et al.MelamineSchiff base/manganese complex with denritic structure:An efficient catalyst for oxidation of alcohols and one-pot synthesis of nitriles[J].Journal of Colloid and Interface Science,2018,527:298-314.
[22]Gamez P,Arends I,Reedijk J,et al.Copper(Ⅱ)-catalysed aerobic oxidation of primary alcohols to aldehydes[J].Chemical Communications,2003,7(19):2414-2415.
[23]Dijksman A,Arends I,Sheldon R.Cu(Ⅱ)-nitroxyl radicals as catalytic galactose oxidase mimics[J].Organic&Biomolecular Chemistry,2003,1:3232-3237.
[24]Hoover J,Ryland B,Stahl S.Copper/TEMPO-catalyzed aerobic alcohol oxidation:Mechanistic assessment of different catalyst systems[J].ACS Catalysis,2013,3(11):2599-2605.
[25]Zhu M,Li B,He P,et al.Oxidant-dependent selective oxidation of alcohols utilizing multinuclear copper-triethanolamine complexes[J].Tetrahedron,2008,64(39):9239-9243.
[26]Gamez P,Arends I,Sheldon R,et al.Room temperature aerobic copper-catalysed selective oxidation of primary alcohols to aldehydes[J].Advanced Synthesis&Catalysis,2004,346(7):805-811.
[27]Kumpulainen E,Koskinen A.Catalytic activity dependency on catalyst components in aerobic copper-TEMPO oxidation[J].Chemistry-A European Journal,2009,15(41):10901-10911.
[28]Ryland B,Mc Cann S,Brunold C,et al.Mechanism of alcohol oxidation mediated by copper(Ⅱ)and nitroxyl radicals[J].Journal of the American Chemical Society,2014,136(34):12166-12173.
[29]Herrerías C,Zhang T,Li C.Catalytic oxidations of alcohols to carbonyl compounds by oxygen under solvent-free and transitionmetal-free conditions[J].Tetrahedron Letters,2006,47(1):13-17.
[30]Yamaguchi K,Mori K,Mizugaki T,et al.Creation of a monomeric Ru species on the surface of hydroxyapatite as an efficient heterogeneous catalyst for aerobic alcohol oxidation[J].Journal of the American Chemical Society,2000,122(29):7144-7145.
[31]Yamaguchi K,Mizuno N.Supported ruthenium catalyst for the heterogeneous oxidation of alcohols with molecular oxygen[J].Angewandte Chemie International Edition,2002,41(23):4538-4542.
[32]Choi E,Lee C,Na Y,et al.[RuCl2(p-cymene)]2 on carbon:An efficient,selective,reusable,and environmentally versatile heterogeneous catalyst[J].Organic Letters,2002,4(14):2369-2371.
[33]Prati L,Rossi M.Gold on carbon as a new catalyst for selective liquid phase oxidation of diols[J].Journal of Catalysis,1998,176(2):552-560.
[34]Bianchi C,Porta F,Prati L,et al.Selective liquid phase oxidation using gold catalysts[J].Topics in Catalysis,2000,13(3):231-236.
[35]Prati L,Martra G.New gold catalysts for liquid phase oxidation[J].Gold Bulletin,1999,32(3):96-101.
[36]Porta F,Prati L,Rossi M,et al.Metal sols as a useful tool for heterogeneous gold catalyst preparation:Reinvestigation of a liquid phase oxidation[J].Catalysis Today,2000,61(1-4):165-172.
[37]Carrettin S,McMorn P,Johnston P,et al.Selective oxidation of glycerol to glyceric acid using a gold catalyst in aqueous sodium hydroxide[J].Chemical Communications,2002,(7):696-697.
[38]Abad A,Concepcion P,Corma A,et al.A collaborative effect between gold and a support induces the selective oxidation of alcohols[J].Angewandte Chemie International Edition,2005,44(26):4066-4069.
[39]Abad A,Almela C,Corma A,et al.Efficient chemoselective alcohol oxidation using oxygen as oxidant.Superior performance of gold over palladium catalysts[J].Tetrahedron,2006,62(28):6666-6672.
[40]Yang X,Wang X,Liang C,et al.Aerobic oxidation of alcohols over Au/TiO2:An insight on the promotion effect of water on the catalytic activity of Au/TiO2[J].Catalysis Communications,2008,9(13):2278-2281.
[41]Tsukamoto D,Shiraishi Y,Sugano Y,et al.Gold nanoparticles located at the interface of anatase/rutile TiO2 particles as active plasmonic photocatalysts for aerobic oxidation[J].Journal of the American Chemical Society,2012,134(14):6309-6315.
[42]Ishida T,Ogihara Y,Ohashi H,et al.Base-free direct oxidation of1-octanol to octanoic acid and its octyl ester over supported gold catalysts[J].Chem Sus Chem,2012,5(11):2243-2248.
[43]Choudhary V,Dhar A,Jana P,et al.A green process for chlorine-free benzaldehyde from the solvent-free oxidation of benzyl alcohol with molecular oxygen over a supported nano-size gold catalyst[J].Green Chemistry,2005,7(11):768-770.
[44]Enache D,Knight D,Hutchings G.Solvent-free oxidation of primary alcohols to aldehydes using supported gold catalysts[J].Catalysis Letters,2005,103(1/2):43-51.
[45]Tsunoyama H,Tsukuda T,Sakurai H.Synthetic application of PVP-stabilized Au nanocluster catalyst to aerobic oxidation of alcohols in aqueous solution under ambient conditions[J].Chemistry Letters,2007,36(2):212-213.
[46]Liu H,Liu Y,Li Y,et al.Metal-organic framework supported gold nanoparticles as a highly active heterogeneous catalyst for aerobic oxidation of alcohols[J].Journal of Physical Chemistry C,2010,114(31):13362-13369.
[47]Beier M,Hansen T,Grunwaldt J D.Selective liquid-phase oxidation of alcohols catalyzed by a silver-based catalyst promoted by the presence of ceria[J].Journal of Catalysis,2009,266(2):320-330.
[48]Korovchenko P,Donze C,Gallezot P,et al.Oxidation of primary alcohols with air on carbon-supported platinum catalysts for the synthesis of aldehydes or acids[J].Catalysis Today,2007,121(1/2):13-21.
[49]Wang T,Shou H,Kou Y,et al.Base-free aqueous-phase oxidation of non-activated alcohols with molecular oxygen on soluble Pt nanoparticles[J].Green Chem,2009,11(4):562-568.
[50]Wang T,Xiao C,Yan L,et al.Aqueous-phase aerobic oxidation of alcohols by soluble Pt nanoclusters in the absence of base[J].Chem Commun,2007,(42):4375-4377.
[51]Yamada Y,Arakawa T,Hocke H,et al.A nanoplatinum catalyst for aerobic oxidation of alcohols in water[J].Angewandte Chemie International Edition,2007,46(5):704-706.
[52]Hong Y,Yan X,Liao X,et al.Platinum nanoparticles supported on Ca(Mg)-zeolites for efficient room-temperature alcohol oxidation under aqueous conditions[J].Chemical Communications,2014,50(68):9679-9682.
[53]Shiraishi Y,Tsukamoto D,Sugano Y,et al.Platinum nanoparticles supported on anatase titanium dioxide as highly active catalysts for aerobic oxidation under visible light irradiation[J].ACS Catalysis,2012,2(9):1984-1992.
[54]Lu T,Du Z,Liu J,et al.Aerobic oxidation of primary aliphatic alcohols over bismuth oxide supported platinum catalysts in water[J].Green Chem,2013,15(8):2215-2221.
[55]Liang D,Gao J,Sun H,et al.Selective oxidation of glycerol with oxygen in a base-free aqueous solution over MWNTs supported Pt catalysts[J].Applied Catalysis B:Environmental,2011,106(3/4):423-432.
[56]Choi K,Akita T,Mizugaki T,et al.Highly selective oxidation of allylic alcohols catalysed by monodispersed 8-shell Pd nanoclusters in the presence of molecular oxygen[J].New Journal of Chemistry,2003,27(2):324-328.
[57]Mori K,Hara T,Mizugaki T,et al.Hydroxyapatite-supported palladium nanoclusters:A highly active heterogeneous catalyst for selective oxidation of alcohols by use of molecular oxygen[J].Journal of the American Chemical Society,2004,126(34):10657-10666.
[58]Pillai U R,Sahle-Demessie E.Selective oxidation of alcohols by molecular oxygen over a Pd/MgO catalyst in the absence of any additives[J].Green Chemistry,2004,6(3):161-165.
[59]Kakiuchi N,Maeda Y,Nishimura T,et al.Pd(Ⅱ)-hydrotalcitecatalyzed oxidation of alcohols to aldehydes and ketones using atmospheric pressure of air[J].Journal of Organic Chemistry,2001,66(20):6620-6625.
[60]Movahed S K,Lehi N F,Dabiri M.Palladium nanoparticles supported on core-shell and yolk-shell Fe3O4@nitrogen doped carbon cubes as a highly efficient,magnetically separable catalyst for the reduction of nitroarenes and the oxidation of alcohols[J].Journal of Catalysis,2018,364:69-79.
[61]Fan J,Dai Y,Li Y,et al.Low-temperature,highly selective,gas-phase oxidation of benzyl alcohol over mesoporous K-Cu-TiO2with stable copper(Ⅰ)oxidation state[J].Journal of the American Chemical Society,2009,131(43):15568-15569.
[62]Dai Y,Yan X,Tang X,et al.Low-temperature gas-phase oxidation of benzyl alcohol on mesoporous K-Cu-TiO2 through oxidative dehydrogenation[J].Chem Cat Chem,2012,4(10):1603-1610.
[63]Anderson R,Griffin K,Johnston P,et al.Selective oxidation of alcohols to carbonyl compounds and carboxylic acids with platinum group metal catalysts[J].Advanced Synthesis&Catalysis,2003,345(4):517-523.
[64]Nie R,Liang D,Shen L,et al.Selective oxidation of glycerol with oxygen in base-free solution over MWCNTs supported PtSb alloy nanoparticles[J].Applied Catalysis B:Environmental,2012,127:212-220.
[65]Dimitratos N,Villa A,Wang D,et al.Pd and Pt catalysts modified by alloying with Au in the selective oxidation of alcohols[J].Journal of Catalysis,2006,244(1):113-121.
[66]Hao Y,Hao G P,Guo D C,et al.Bimetallic Au-Pd nanoparticles confined in tubular mesoporous carbon as highly selective and reusable benzyl alcohol oxidation catalysts[J].Chem Cat Chem,2012,4(10):1595-1602.
[67]Zhang H,Xie Y,Sun Z,et al.In-situ loading ultrafine AuPd particles on ceria:highly active catalyst for solvent-free selective oxidation of benzyl alcohol[J].Langmuir,2011,27(3):1152-1157.
[68]Wang D,Villa A,Spontoni P,et al.In situ formation of Au-Pd bimetallic active sites promoting the physically mixed monometallic catalysts in the liquid-phase oxidation of alcohols[J].Chemistry-AEuropean Journal,2010,16(33):10007-10013.
[69]Chen Y,Lim H,Tang Q,et al.Solvent-free aerobic oxidation of benzyl alcohol over Pd monometallic and Au-Pd bimetallic catalysts supported on SBA-16 mesoporous molecular sieves[J].Applied Catalysis A:General,2010,380(1/2):55-65.
[70]Liotta L F,Vanezia A M,Deganello G,et al.Liquid phase selective oxidation of benzyl alcohol over Pd-Ag catalysts supported on pumice[J].Catalysis Today,2001,66(2/3/4):271-276.
[71]Enache D I,Edwards J K,Landon P,et al.Solvent-free oxidation of primary alcohols to aldehydes using Au-Pd/TiO2 catalysts[J].Science,2006,311:362-365.
[72]Ebitani K,Ji H B,Mizugaki T,et al.Highly active trimetallic Ru/CeO2/CoO(OH)catalyst for oxidation of alcohols in the presence of molecular oxygen[J].Journal of Molecular Catalysis A:Chemical,2004,212(1/2):161-170.
[73]Liu G,Liu J,Li W,et al.Aerobic oxidation of alcohols over Ru-Mn-Ce and Ru-Co-Ce catalysts:The effect of calcination temperature[J].Applied Catalysis A:General,2017,535:77-84.
[74]Kawabata T,Shinozuka Y,Ohishi Y,et al.Nickel containing Mg-Al hydrotalcite-type anionic clay catalyst for the oxidation of alcohols with molecular oxygen[J].Journal of Molecular Catalysis A:Chemical,2005,236(1/2):206-215.
[75]Bora U,Chaudhuri M K,Dey D,et al.3,5-Dimethylpyrazolium fluorochromate(Ⅵ),C5H8N2H[CrO3F],(DmpzHFC):A convenient new reagent for oxidation of organic substrates[J].Tetrahedron,2001,57(12):2445-2448.
[76]Ragupathi C,Vijaya J J,Kumar R T,et al.Selective liquid phase oxidation of benzyl alcohol catalyzed by copper aluminate nanostructures[J].Journal of Molecular Structure,2015,1079:182-188.
[77]Maiti S K,Banerjee S,Mukherjee A K,et al.Oxoperoxo molybdenum(Ⅵ)and tungsten(Ⅵ)and oxodiperoxo molybdate(Ⅵ)and tungstate(Ⅵ)complexes with 8-quinolinol:Synthesis,structure and catalytic activity[J].New Journal of Chemistry,2005,29(4):554-563.
[78]Luan Y,Wang G,Luck R L,et al.Oxidation of alcohols with hydrogen peroxide catalyzed by molybdenum(Ⅵ)-peroxo complex under solvent-free conditions[J].Chemistry Letters,2007,36(10):1236-1237.
[79]Noyori R,Aoki M,Sato K.Green oxidation with aqueous hydrogen peroxide[J].Chemical Communications,2003,(16):1977-1986.
[80]Wang J,Yan L,Li G,et al.Mono-substituted Keggin-polyoxometalate complexes as effective and recyclable catalyst for the oxidation of alcohols with hydrogen peroxide in biphasic system[J].Tetrahedron Letters,2005,46(41):7023-7027.
[81]Guo M L,Li H Z.Selective oxidation of benzyl alcohol to benzaldehyde with hydrogen peroxide over tetra-alkylpyridinium octamolybdate catalysts[J].Green Chemistry,2007,9(5):421-423.
[82]Martín S E,Garrone A.Efficient solvent-free iron(Ⅲ)catalyzed oxidation of alcohols by hydrogen peroxide[J].Tetrahedron Letters,2003,44(3):549-552.
[83]Tanaka S,Kon Y,Nakashima T,et al.Chemoselective hydrogen peroxide oxidation of allylic and benzylic alcohols under mild reaction conditions catalyzed by simple iron-picolinate complexes[J].RSC Advances,2014,4(71):37674-37678.
[84]Chàvez J E,Crotti C,Zangrando E,et al.Iron complexes with nitrogen bidentate ligands as green catalysts for alcohol oxidation[J].Journal of Molecular Catalysis A:Chemical,2016,421:189-195.
[85]Balogh-Hergovich E,Speier G.Catalytic oxidation of alcohols to carbonyl compounds with hydrogen peroxide using dinuclear iron complexes[J].Journal of Molecular Catalysis A:Chemical,2005,230:79-83.
[86]Crotti C,Farnetti E.Selective oxidation of glycerol catalyzed by iron complexes[J].Journal of Molecular Catalysis A:Chemical,2015,396:353-359.
[87]Lenze M,Sedinkin S L,Bauer E B.Polydentate pyridyl ligands and the catalytic activity of their iron(Ⅱ)complexes in oxidation reactions utilizing peroxides as the oxidants[J].Journal of Molecular Catalysis A:Chemical,2013,373:161-171.
[88]Shejwalkar P,Rath N P,Bauer E B.New iron(Ⅱ)a-iminopyridine complexes and their catalytic activity in the oxidation of activated methylene groups and secondary alcohols to ketones[J].Dalton Transactions,2011,40(29):7617-7631.
[89]Panda C,Ghosh M,Panda T,et al.Fe(Ⅲ)complex of biuret-amide based macrocyclic ligand as peroxidase enzyme mimic[J].Chemical Communications,2011,47(28):8016-8018.
[90]Mardani H R,Golchoubian H.Effective oxidation of benzylic and aliphatic alcohols with hydrogen peroxide catalyzed by a manganese(Ⅲ)Schiff-base complex under solvent-free conditions[J].Tetrahedron Letters,2006,47(14):2349-2352.
[91]Velusamy S,Punniyamurthy T.Copper(Ⅱ)-catalyzed oxidation of alcohols to carbonyl compounds with hydrogen peroxide[J].European Journal of Organic Chemistry,2003,2003(20):3913-3915.
[92]Karthikeyan P,Aswar S A,Muskawar P N,et al.A novel CuCl2/BILcatalyst for direct oxidation of alcohol to acid at ambient temperature[J].Catalysis Communications,2012,26:189-193.
[93]Kon Y,Usui Y,Sato K.Oxidation of allylic alcohols toα,β-unsaturated carbonyl compounds with aqueous hydrogen peroxide under organic solvent-free conditions[J].Chemical Communications,2007,(42):4399-4400.
[94]Ni J,Yu W J,He L,et al.A green and efficient oxidation of alcohols by supported gold catalysts using aqueous H2O2 under organic solvent-free conditions[J].Green Chemistry,2009,11(6):756-759.
[95]Pillai U R,Sahle-Demessie E.Oxidation of alcohols over Fe3+/montmorillonite-K10 using hydrogen peroxide[J].Applied Catalysis A:General,2003,245(1):103-109.
[96]Cang R,Lu B,Li X,et al.Iron-chloride ionic liquid immobilized on SBA-15 for solvent-free oxidation of benzyl alcohol to benzaldehyde with H2O2[J].Chemical Engineering Science,2015,137:268-275.
[97]Qi L,Qi X,Wang J,et al.A synergistic effect in the combination of H2O2,FeAPO-5 and NaBr for selective oxidation of benzyl alcohols[J].Catalysis Communications,2011,16(1):225-228.
[98]Shi F,Tse M K,Pohl M M,et al.Nano-iron oxide-catalyzed selective oxidations of alcohols and olefins with hydrogen peroxide[J].Journal of Molecular Catalysis A:Chemical,2008,292(1/2):28-35.
[99]Ragupathi C,Vijaya J J,Kumar R T,et al.Selective liquid phase oxidation of benzyl alcohol catalyzed by copper aluminate nanostructures[J].Journal of Molecular Structure,2015,1079:182-188.
[100]Nasrollahzadeh M,Bagherzadeh M,Karimi H.Preparation,characterization and catalytic activity of CoFe2O4 nanoparticles as a magnetically recoverable catalyst for selective oxidation of benzyl alcohol to benzaldehyde and reduction of organic dyes[J].Journal of Colloid and Interface Science,2016,465:271-278.
[101]Wang X,Wu G,Li J,et al.Surface-modified improvement in catalytic performance of Cr(salen)complexes immobilized on MCM-41 in solvent-free selective oxidation of benzyl alcohol[J].Catalysis Letters,2007,119:87-94.
[102]Wagh R B,Nagarkar J M.An efficient and sustainable protocol for oxidation of alcohols to carbonyl compounds[J].Tetrahedron Letters,2018,59(37):3443-3447.
[103]Ajjou A N.First example of water-soluble transition-metal catalysts for Oppenauer-type oxidation of secondary alcohols[J].Tetrahedron Letters,2001,42(1):13-15.
[104]Hanasaka F,Fujita K,Yamaguchi R.Synthesis of new cationic Cp*Ir N-heterocyclic carbene complexes and their high catalytic activities in the Oppenauer-type oxidation of primary and secondary alcohols[J].Organometallics,2005,24(14):3422-3433.
[105]Fujita K,Furukawa S,Yamaguchi R.Oxidation of primary and secondary alcohols catalyzed by a pentamethylcyclopentadienyliridium complex[J].Journal of Organometallic Chemistry,2002,649(2):289-292.
[106]Moyer S A,Funk T W.Air-stable iron catalyst for the Oppenauertype oxidation of alcohols[J].Tetrahedron Letters,2010,51(41):5430-5433.
[107]Coleman M G,Brown A N,Bolton B A,et al.Iron-catalyzed Oppenauer-type oxidation of alcohols[J].Advanced Synthesis&Catalysis,2010,352(6):967-970.