Selective Oxidation of Alcohols to Carbonyl Compounds over Metalloporphyrins with MgAl Hydrotalcite Additive
- Corresponding author: CHEN Chuan, 8000000705@czie.edu.cn XUE Xuming, 8000000664@czie.edu.cn
Citation:
CHEN Chuan, XU Yingdi, XUE Xuming, ZHOU Pengpeng. Selective Oxidation of Alcohols to Carbonyl Compounds over Metalloporphyrins with MgAl Hydrotalcite Additive[J]. Chinese Journal of Applied Chemistry,
;2019, 36(11): 1286-1293.
doi:
10.11944/j.issn.1000-0518.2019.11.190073
Caron S, Dugger R W, Ruggeri S G. Large-Scale Oxidations in the Pharmaceutical Industry[J]. Chem Rev, 2006,106(7):2943-2989. doi: 10.1021/cr040679f
CHUN Chaosen, WANG Xiaoli, HU Yutao. Catalyzed Oxidation of Alcohols by 2, 2, 6, 6-Tetramethyl-1-iperidinyloxy with Sodium Bromate and Ferric Chloride as Accelorators[J]. Chinese J Appl Chem, 2015,32(6):666-670.
Gualteros J A D, Garcia M A S, da Silva A G M. Synthesis of Highly Dispersed Gold Nanoparticles on Al2O3, SiO2, and TiO2 for the Solvent-free Oxidation of Benzyl Alcohol under Low Metal Loadings[J]. J Mater Sci, 2019,54(1):238-251. doi: 10.1007/s10853-018-2827-x
Hao B C, Xiao M, Wang Y J. Recyclable Amphiphilic Metal Nanoparticle Colloid Enabled Atmospheric Oxidation of Alcohols[J]. ACS Appl Mater Interfaces, 2018,10(40):34332-34339. doi: 10.1021/acsami.8b12989
Ke C X, Li M Y, Fan G L. Pt Nanoparticles Supported on Nitrogen-Doped-Carbon-Decorated CeO2 for Base-Free Aerobic Oxidation of 5-Hydroxymethylfurfural[J]. Chem-Asian J, 2018,13(18):2714-2722. doi: 10.1002/asia.201800738
Iwahama T, Yoshino Y, Keitoku T. Efficient Oxidation of Alcohols to Carbonyl Compounds with Molecular Oxygen Catalyzed by N-Hydroxyphthalimide Combined with a Co Species[J]. J Org Chem, 2000,65(20):6502-6507. doi: 10.1021/jo000760s
Chen B, Li J, Yang G. Aerobic Oxidation of Benzyl Alcohols Using a Novel Combination of N-Hydroxyphthalimide(NHPI) with HNO3 and CuBr2[J]. Res Chem Intermed, 2015,41(6):3929-3936. doi: 10.1007/s11164-013-1500-x
SUN Bin. H2O2 Oxidation of Alcohols in Water by in situ Made Water Soluble Salen-Cu Complex[J]. Chem Res Appl, 2019,31(1):128-133. doi: 10.3969/j.issn.1004-1656.2019.01.020
Saha T, Pramanick R, Sengupta D. Metal-Ligand Cooperativity in a Ruthenium(Ⅱ) Complex of Bis-azoaromatic Ligand for Catalytic Dehydrogenation of Alcohols[J]. Inorg Chim Acta, 2019,484:160-166. doi: 10.1016/j.ica.2018.09.038
LIU Lin, MA Juanjuan, FU Tingming. Selective Aerobic Oxidation of Alcohols Catalyzed by Octahedral Molecular Sieves in Ionic Liquids[J]. Chinese J Appl Chem, 2010,27(7):801-805.
CHEN Chuan, XUE Xuming. Selective Oxidation of Alcohol to Aldehyde Catalyzed by Mg Modified NiGa Hydrotalcite-like Compounds[J]. Fine Chem, 2018,35(11):1900-1904, 1941.
Meng L Y, Zhai S R, Li S. Synthesis and Characterization of Tungstophosphoric Acid/Pentaethylenehexamine/ZrSBA-15 and Its Use in the Selective Oxidation of Benzyl Alcohol under Solvent-free Conditions[J]. Eur J Inorg Chem, 2014,2014(14):2337-2344. doi: 10.1002/ejic.201402028
SU Hao, YANG Chun. Selective Oxidation of Benzyl Alcohol Catalyzed by Polyoxometalates:A Green Recyclable Catalytic System with High Performance[J]. Chinese J Appl Chem, 2014,31(8):958-964.
Otake K I, Cui Y X, Buru C T. Single-atom-based Vanadium Oxide Catalysts Supported on Metal Organic Frameworks:Selective Alcohol Oxidation and Structure Activity Relationship[J]. J Am Chem Soc, 2018,140(28):8652-8656. doi: 10.1021/jacs.8b05107
Zhan G W, Fan L, Zhou S F. Fabrication of Integrated Cu@HKUST-1@Au Nanocatalysts via Galvanic Replacements Toward Alcohols Oxidation Application[J]. ACS Appl Mater Interfaces, 2018,10(41):35234-35243. doi: 10.1021/acsami.8b12380
LIU Lin, WEI Yunyang, YUE Caibo. Oxidation of Alcohols to Corresponding Aldehydes and Ketones with Molecular Oxygen Catalyzed by Task-Specific Ionic Liquid[J]. Chinese J Appl Chem, 2007,24(11):1327-1331. doi: 10.3969/j.issn.1000-0518.2007.11.022
Wagh R B, Nagarkar J M. An Efficient and Sustainable Protocol for Oxidation of Alcohols to Carbonyl Compounds[J]. Tetrahedron Lett, 2018,59(37):3443-3447. doi: 10.1016/j.tetlet.2018.08.011
Kuttassery F, Mathew S, Remello S N. Alternative Route to Bypass the Bottle-Neck of Water Oxidation:Two-Electron Oxidation of Water Catalyzed by Earth-Abundant Metalloporphyrins[J]. Coordin Chem Rev, 2018,377:64-72. doi: 10.1016/j.ccr.2018.08.027
Calvete M J F, Pineiro M, Dias L D. Hydrogen Peroxide and Metalloporphyrins in Oxidation Catalysis:Old Dogs with Some New Tricks[J]. ChemCatChem, 2018,10(17):3615-3635. doi: 10.1002/cctc.201800587
Kato C N, Ono M, Hino T. Room Temperature Oxidation of Alcohols with 1 atm Dioxygen and Air Catalyzed by a Novel Three-Dimensional Microporous Ruthenium(Ⅱ, Ⅲ), 4', 4″, 4'″-(21H, 23H-Porphine-5, 10, 15, 20-tetrayl)tetrakisbenzoate Tetrafluoroborate[J]. Catal Commun, 2006,7(9):673-677. doi: 10.1016/j.catcom.2006.02.011
Ji H B, Yuan Q L, Zhou X T. Highly Efficient Selective Oxidation of Alcohols to Carbonyl Compounds Catalyzed by Ruthenium(Ⅲ) meso-Tetraphenylporphyrin Chloride in the Presence of Molecular Oxygen[J]. Bioorg Med Chem Lett, 2007,17(22):6364-6368. doi: 10.1016/j.bmcl.2007.08.063
Korotchenko V N, Severin K, Gagné M R. The Aerobic Oxidation of Alcohols with a Ruthenium Porphyrin Catalyst in Organic and Fluorinated Solvents[J]. Org Biomol Chem, 2008,6(11):1961-1965. doi: 10.1039/b800583d
Liu L H, Yu M M, Wayland B B. Aerobic Oxidation of Alcohols Catalyzed by Rhodium(Ⅲ) Porphyrin Complexes in Water:Reactivity and Mechanistic Studies[J]. Chem Commun, 2010,46(34):6353-6355. doi: 10.1039/c0cc01406k
Sun C G, Hu B C, Liu Z L. Rapid Aerobic Oxidation of Alcohols to Carbonyl Compounds with Dioxygen Using Metallodeuteroporphyrin Dimethyl Esters as Catalysts in the Presence of Isobutylaldehyde[J]. Heteroatom Chem, 2012,23:295-303. doi: 10.1002/hc.21017
Rahimi R, Gholamrezapor E, Naimi-jamal M R. Oxidation of Benzyl Alcohols to the Corresponding Carbonyl Compounds Catalyzed by Copper(Ⅱ) meso-Tetraphenyl Porphyrin as Cytochrome P-450 Model Reaction[J]. Inorg Chem Commun, 2011,14(10):1561-1568. doi: 10.1016/j.inoche.2011.05.056
Egami H, Shimizu H, Katsuki T. Aerobic Oxidation of Primary Alcohols in the Presence of Activated Secondary Alcohols[J]. Tetrahedron Lett, 2005,46(5):783-786. doi: 10.1016/j.tetlet.2004.12.010
Liu S J, Zhang M, Lu R. Sodium Copper Chlorophyllin Catalyzed Chemoselective Oxidation of Benzylic Alcohols and Diarylmethanes in Water[J]. Molecules, 2018,23(8):1883-1889. doi: 10.3390/molecules23081883
Li Y J, Sun B S, Yang W J. Synthesis of Conjugated Mn Porphyrin Polymers with p-Phenylenediamine Building Blocks and Efficient Aerobic Catalytic Oxidation of Alcohols[J]. Appl Catal A:Gen, 2016,515:164-169. doi: 10.1016/j.apcata.2016.02.003
Zhou W Y, Tian P, Sun F A. Highly Efficient Transformation of Alcohol to Carbonyl Compounds under a Hybrid Bifunctional Catalyst Originated from Metalloporphyrins and Hydrotalcite[J]. J Catal, 2016,335:105-116. doi: 10.1016/j.jcat.2015.11.017
Sun F A, Zhou J C, Zhou W Y. Efficient Aerobic Oxidation of Alcohols Catalyzed by NiGa Hydrotalcites in the Absence of Any Additives[J]. New J Chem, 2018,42:4029-4235. doi: 10.1039/C7NJ03895J
Zhou W Y, Tao Q Y, Pan J G. Effect of Basicity on the Catalytic Properties of Ni-Containing Hydrotalcites in the Aerobic Oxidation of Alcohol[J]. J Mol Catal A Chem, 2016,425:255-265. doi: 10.1016/j.molcata.2016.10.017
Demel J, Lang K. Layered Hydroxide-Porphyrin Hybrid Materials:Synthesis, Structure, and Properties[J]. Eur J Inorg Chem, 2012(32):5154-5164.
Lyons J E, Ellis Jr P E, Myers Jr H K. Halogenated Metalloporphyrin Complexes as Catalysts for Selective Reactions of Acyclic Alkanes with Molecular Oxygen[J]. J Catal, 1995,155(1):59-73. doi: 10.1006/jcat.1995.1188
Kameyama H, Narumi F, Hattori T. Oxidation of Cyclohexene with Molecular Oxygen Catalyzed by Cobalt Porphyrin Complexes Immobilized on Montmorillonite[J]. J Mol Catal A Chem, 2006,258(1/2):172-177.
SerraAntónio A C, Gonsalves M A R. Mild Oxygen Activation with Isobutyraldehyde Promoted by Simple Salts[J]. Tetrahedron Lett, 2011,52(27):3489-3491. doi: 10.1016/j.tetlet.2011.04.120
Wentzel B B, Alsters P L, Feiters M C. Mechanistic Studies on the Mukaiyama Epoxidation[J]. J Org Chem, 2004,69(10):3453-3464. doi: 10.1021/jo030345a
Zhou W Y, Sun C G, Xu S C. Metallo-deuteroporphyrin as a Novel Catalyst for p-Xylene Oxidation Using Molecular Oxygen[J]. Inorg Chim Acta, 2012,382:167-170. doi: 10.1016/j.ica.2011.12.039
Tagliatesta P, Giovannetti D, Leoni A. Manganese(Ⅲ) Porphyrins as Catalysts for the Oxidation of Aromatic Substrates:An Insight into the Reaction Mechanism and the Role of the Cocatalyst[J]. J Mol Catal A Chem, 2006,252(1/2):96-102.
Xinhao Yan , Guoliang Hu , Ruixi Chen , Hongyu Liu , Qizhi Yao , Jiao Li , Lingling Li . Polyethylene Glycol-Ammonium Sulfate-Nitroso R Salt System for the Separation of Cobalt (II). University Chemistry, 2024, 39(6): 287-294. doi: 10.3866/PKU.DXHX202310073
Peng YUE , Liyao SHI , Jinglei CUI , Huirong ZHANG , Yanxia GUO . Effects of Ce and Mn promoters on the selective oxidation of ammonia over V2O5/TiO2 catalyst. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 293-307. doi: 10.11862/CJIC.20240210
Zhanggui DUAN , Yi PEI , Shanshan ZHENG , Zhaoyang WANG , Yongguang WANG , Junjie WANG , Yang HU , Chunxin LÜ , Wei ZHONG . Preparation of UiO-66-NH2 supported copper catalyst and its catalytic activity on alcohol oxidation. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 496-506. doi: 10.11862/CJIC.20230317
Shihui Shi , Haoyu Li , Shaojie Han , Yifan Yao , Siqi Liu . Regioselectively Synthesis of Halogenated Arenes via Self-Assembly and Synergistic Catalysis Strategy. University Chemistry, 2024, 39(5): 336-344. doi: 10.3866/PKU.DXHX202312002
Yunhao Zhang , Yinuo Wang , Siran Wang , Dazhen Xu . Progress in Selective Construction of Functional Aromatics from Nitrogenous Cycloalkanes. University Chemistry, 2024, 39(11): 136-145. doi: 10.3866/PKU.DXHX202401083
Peiran ZHAO , Yuqian LIU , Cheng HE , Chunying DUAN . A functionalized Eu3+ metal-organic framework for selective fluorescent detection of pyrene. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 713-724. doi: 10.11862/CJIC.20230355
Xilin Zhao , Xingyu Tu , Zongxuan Li , Rui Dong , Bo Jiang , Zhiwei Miao . Research Progress in Enantioselective Synthesis of Axial Chiral Compounds. University Chemistry, 2024, 39(11): 158-173. doi: 10.12461/PKU.DXHX202403106
Conghao Shi , Ranran Wang , Juli Jiang , Leyong Wang . The Illustration on Stereoisomers of Macrocycles Containing Multiple Chiral Centers via Tröger Base-based Macrocycles. University Chemistry, 2024, 39(7): 394-397. doi: 10.3866/PKU.DXHX202311034
Jiakun BAI , Ting XU , Lu ZHANG , Jiang PENG , Yuqiang LI , Junhui JIA . A red-emitting fluorescent probe with a large Stokes shift for selective detection of hypochlorous acid. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1095-1104. doi: 10.11862/CJIC.20240002
Jun LUO , Baoshu LIU , Yunchang ZHANG , Bingkai WANG , Beibei GUO , Lan SHE , Tianheng CHEN . Europium(Ⅲ) metal-organic framework as a fluorescent probe for selectively and sensitively sensing Pb2+ in aqueous solution. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2438-2444. doi: 10.11862/CJIC.20240240
Hailian Tang , Siyuan Chen , Qiaoyun Liu , Guoyi Bai , Botao Qiao , Fei Liu . Stabilized Rh/hydroxyapatite Catalyst for Furfuryl Alcohol Hydrogenation: Application of Oxidative Strong Metal-Support Interactions in Reducing Conditions. Acta Physico-Chimica Sinica, 2025, 41(4): 100036-. doi: 10.3866/PKU.WHXB202408004
Lijuan Wang , Yuping Ning , Jian Li , Sha Luo , Xiongfei Luo , Ruiwen Wang . Enhancing the Advanced Nature of Natural Product Chemistry Laboratory Courses with New Research Findings: A Case Study of the Application of Berberine Hydrochloride in Photodynamic Antimicrobial Films. University Chemistry, 2024, 39(11): 241-250. doi: 10.12461/PKU.DXHX202403017
Jie ZHAO , Sen LIU , Qikang YIN , Xiaoqing LU , Zhaojie WANG . Theoretical calculation of selective adsorption and separation of CO2 by alkali metal modified naphthalene/naphthalenediyne. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 515-522. doi: 10.11862/CJIC.20230385
Junjie Zhang , Yue Wang , Qiuhan Wu , Ruquan Shen , Han Liu , Xinhua Duan . Preparation and Selective Separation of Lightweight Magnetic Molecularly Imprinted Polymers for Trace Tetracycline Detection in Milk. University Chemistry, 2024, 39(5): 251-257. doi: 10.3866/PKU.DXHX202311084
Yiling Wu , Peiyao Jin , Shenyue Tian , Ji Zhang . The Star of Sugar Substitutes: An Interview of Erythritol. University Chemistry, 2024, 39(9): 22-27. doi: 10.12461/PKU.DXHX202404034
Yinuo Wang , Siran Wang , Yilong Zhao , Dazhen Xu . Selective Synthesis of Diarylmethyl Anilines and Triarylmethanes via Multicomponent Reactions: Introduce a Comprehensive Experiment of Organic Chemistry. University Chemistry, 2024, 39(8): 324-330. doi: 10.3866/PKU.DXHX202401063
Yan LIU , Jiaxin GUO , Song YANG , Shixian XU , Yanyan YANG , Zhongliang YU , Xiaogang HAO . Exclusionary recovery of phosphate anions with low concentration from wastewater using a CoNi-layered double hydroxide/graphene electronically controlled separation film. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1775-1783. doi: 10.11862/CJIC.20240043
Yifeng TAN , Ping CAO , Kai MA , Jingtong LI , Yuheng WANG . Synthesis of pentaerythritol tetra(2-ethylthylhexoate) catalyzed by h-MoO3/SiO2. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2155-2162. doi: 10.11862/CJIC.20240147
Limei CHEN , Mengfei ZHAO , Lin CHEN , Ding LI , Wei LI , Weiye HAN , Hongbin WANG . Preparation and performance of paraffin/alkali modified diatomite/expanded graphite composite phase change thermal storage material. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 533-543. doi: 10.11862/CJIC.20230312
Zhilian Liu , Wengui Wang , Hongxiao Yang , Yu Cui , Shoufeng Wang . Ideological and Political Education Design for the Synthesis of Irinotecan Drug Intermediate 7-Ethyl Camptothecin. University Chemistry, 2024, 39(2): 89-93. doi: 10.3866/PKU.DXHX202306012
Reaction conditions:benzyl alcohol 1 mmol, acetonitrile 2 mL, catalyst 5 mg, IBA 3 mmol, MgAl-HT 12 mg, 60 ℃, oxygen atmosphere
Reaction conditions:benzyl alcohol 1 mmol, acetonitrile 2 mL, CoTPP 5 mg, IBA 3 mmol, MgAl-HT 12 mg, 1.5 h, oxygen atmosphere
Reaction conditions:benzyl alcohol 1 mmol, acetonitrile 2 mL, CoTPP 5 mg, IBA 3 mmol, base 12 mg, 60 ℃, 1.5 h, oxygen atmosphere
Reaction conditions: benzyl alcohol 1 mmol, acetonitrile 2 mL, CoTPP 5 mg, MgAl-HT 12 mg, 60 ℃, oxygen atmosphere a.1:1; b.2:1; c.3:1; d.4:1; e.5:1; f.6:1
Reaction conditions:benzyl alcohol 1 mmol, acetonitrile 2 mL, CoTPP 5 mg, MgAl-HT, IBA 5 mmol, 60 ℃, oxygen atmosphere