Highly Efficient Aerobic Oxidation of Arylalkanes with a Biomimetic Catalyst Platform

doi:10.11944/j.issn.1000-0518.2017.09.170191

Chinese Journal of Applied Chemistry ›› 2017, Vol. 34 ›› Issue (9): 1079-1085.DOI: 10.11944/j.issn.1000-0518.2017.09.170191

• Full Papers • Previous Articles Next Articles

Highly Efficient Aerobic Oxidation of Arylalkanes with a Biomimetic Catalyst Platform

XU Kerui,ZHONG Zhiming,XU Huidong,WANG Xuan,ZHAO Min,WU Chuande()

State Key Laboratory of Silicon Materials,Department of Chemistry, Zhejiang University,Hangzhou 310027,China

Received:2017-06-02 Accepted:2017-06-27 Published:2017-08-31 Online:2017-08-31
Contact: XU Kerui,ZHONG Zhiming,XU Huidong,WU Chuande
Supported by:
Supported by the National Natural Science Foundation of China(No.21373180, No.21525312), the Fundamental Research Funds for the Central Universities(No.2017XZZX001-03A, No.2017FZA3007)

Abstract

Abstract:

It is a challenge to oxidize inert hydrocarbons with molecular oxygen, which can be easily realized by enzymes under mild conditions. Inspired by the catalytic mechanism of enzymes, we used the composite material CuPW₁₁@HKUST-1, consisting of encapsulated Keggin-type polyoxometalate [CuPW₁₁O₃₉]^5-(abbreviated as CuPW₁₁) in the pore space of metal-organic framework HKUST-1, as a redox catalyst, and N-hydroxyphthalimide(NHPI) as a co-catalyst, for the biomimetic aerobic oxidation of arylalkanes under mild conditions. The biomimetic system exhibits enzyme-like features of high efficiency and high selectivity in the aerobic oxidation of arylalkanes by imitating the structural features, active sites and catalytic mechanism of enzymes, in which up to 99% yield and 17700 turnover number(TON) have been realized in the aerobic oxidation reaction. This work offers a feasible pathway for highly efficient aerobic oxidation of inert organic molecules under mild conditions.

Key words: biomimetic catalysis, metal-organic frameworks, polyoxometalates, synergistic catalysis

XU Kerui, ZHONG Zhiming, XU Huidong, WANG Xuan, ZHAO Min, WU Chuande. Highly Efficient Aerobic Oxidation of Arylalkanes with a Biomimetic Catalyst Platform[J]. Chinese Journal of Applied Chemistry, 2017, 34(9): 1079-1085.

References

[1]	Hughes M D,Xu Y J,Jenkins P,et al.Tunable Gold Catalysts for Selective Hydrocarbon Oxidation Under Mild Conditions[J]. Nature,2005,437(7062):1132-1135.
[2]	Liese A,Seelbach K,Eds. Industrial Biotransformations[M]. Wandrey,C. Wiley-VCH,Weinhiem,2006.
[3]	Faber K. Biotransformations in Organic Chemistry[M]. Springer-Verlag,Berlin,5th ed,2004.
[4]	Kadish K M,Smith K M,Guilard R,Eds. The Porphyrin Handbook[M]. Academic Press,San Diego,2000.
[5]	Sheldon R A. Metalloporphyrins in Catalytic Oxidation[M]. Marcel Dekker,Basel,1994.
[6]	Wang S S,Yang G Y. Recent Advances in Polyoxometalate-Catalyzed Reactions[J]. Chem Rev,2015,115(11):4893-4962.
[7]	Ye J J,Wu C D. Immobilization of Polyoxometalates in Crystalline Solids for Highly Efficient Heterogeneous Catalysis[J]. Dalton Trans,2016,45(25):10101-10112.
[8]	Zhou H C,Long J R,Yaghi O M. Metal-Organic Frameworks Special Issue[J]. Chem Rev,2012,112(2):673-1268.
[9]	Zhou H C,Kitagawa S. Themed Issues on Metal-Organic Frameworks[J]. Chem Soc Rev,2014,43(16):5415-6172.
[10]	Zhao M,Ou S,Wu C D. Porous Metal-Organic Frameworks for Heterogeneous Biomimetic Catalysis[J]. Acc Chem Res,2014,47(4):1199-1207.
[11]	Zou C,Zhang Z,Xu X,et al.A Multifunctional Organic-Inorganic Hybrid Structure Based on MnIII-Porphyrin and Polyoxometalate as a Highly Effective Dye Scavenger and Heterogenous Catalyst[J]. J Am Chem Soc,2012,134(1):87-90.
[12]	Yang X L,Xie M H,Zou C,et al.Porous Metalloporphyrinic Frameworks Constructed from Metal 5,10,15,20-Tetrakis(3,5-biscarboxylphenyl)porphyrin for Highly Efficient and Selective Catalytic Oxidation of Alkylbenzenes[J]. J Am Chem Soc,2012,134(25):10638-10645.
[13]	Liu J,Chen L,Cui H,et al.Applications of Metal Organic Frameworks in Heterogeneous Supramolecular Catalysis[J]. Chem Soc Rev,2014,43(16):6011-6061.
[14]	Ou S,Wu C D. Rational Construction of Metal-Organic Frameworks for Heterogeneous Catalysis[J]. Inorg Chem Front,2014,1(10):721-734.
[15]	Wu C D,Zhao M. Incorporation of Molecular Catalysts in Metal Organic Frameworks for Highly Efficient Heterogeneous Catalysis[J]. Adv Mater,2017,29(14):1605446.
[16]	Liu Y,Liu S,He D,et al.Crystal Facets Make a Profound Difference in Polyoxometalate-Containing Metal-Organic Frameworks as Catalysts for Biodiesel Production[J]. J Am Chem Soc,2015,137(39):12697-12703.
[17]	Sun C Y,Liu S X,Liang D D,et al.Highly Stable Crystalline Catalysts Based on a Microporous Metal-Organic Framework and Polyoxometalates[J]. J Am Chem Soc,2009,131(5):1883-1888.
[18]	Zhao M,Ou S,Wu C D. Biomimetic Activation of Molecular Oxygen with a Combined Metalloporphyrinic Framework and Co-catalyst Platform[J]. ChemCatChem,2017,9(3):1192-1196.
[19]	Chui S S Y,Lo S M F,Charmant J P H,et al. A Chemically Functionalizable Nanoporous Material [Cu3(TMA)2(H2O)3]n[J]. Science,1999,283(5405):1148-1150.
[20]	Song J,Luo Z,Britt D K,et al.A Multiunit Catalyst with Synergistic Stability and Reactivity:A Polyoxometalate Metal Organic Framework for Aerobic Decontamination[J]. J Am Chem Soc,2011,133(42):16839-16846.
[21]	Tourn C M,Tourn G F,Malik S A,et al.Triheteropolyanions Containing Copper(Ⅱ), Manganese(Ⅱ), or Manganese(Ⅲ)[J]. J Inorg Nucl Chem,1970,32(12):3875-3890.
[22]	Labinger J A,Bercaw J E. Understanding and Exploiting C—H Bond Activation[J]. Nature,2002,417(6888):507-514.
[23]	Bäckvall J E. Modern Oxidation Methods[M]. John Wiley,Weinheim,2011.
[24]	Recupero F C,Punta F. Free Radical Functionalization of Organic Compounds Catalyzed by N-Hydroxyphthalimide[J]. Chem Rev,2007,107(9):3800-3842.

Highly Efficient Aerobic Oxidation of Arylalkanes with a Biomimetic Catalyst Platform

RichHTML

PDF

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Xue-Bo LEI, Hui-Jing LIU, He-Yu DING, Guo-Dong SHEN, Run-Jun SUN. Research Progress on Photocatalysts for Degradation of Organic Pollutants in Printing and Dyeing Wastewater [J]. Chinese Journal of Applied Chemistry, 2023, 40(5): 681-696.
[2]	Ye LIU, Shao-Bo GUO, Yan-Li LIANG, Hong-Guang GE, Jian-Qi MA, Zhi-Feng LIU, Bo LIU. Preparation and Catalytic Performance of Core‑Shell CuFe₂O₄@NH₂@Pt Nanocomposites [J]. Chinese Journal of Applied Chemistry, 2022, 39(8): 1237-1245.
[3]	ZHANG Ming-Shan, LI Teng-Ya, LEI Yu, WU Yan, HE Shu-Hai. Determination of Two Sulfonamides in Environmental Water Based on Dispersivesolid-Phase Extraction with MIL-101(Cr) Metal-Organic Framework [J]. Chinese Journal of Applied Chemistry, 2021, 38(2): 236-244.
[4]	WU Qiu-Ping, CAI Kun-Ting, WANG Yuan-Kang, SUN Kai, YANG Jin-Bo, HAN Song-Bai, LIU Yun-Tao. Microwave Absorption Properties of Co/C and Microwave-Heat Conversion Properties of Co/C-Polyurethane Phase Change Composites [J]. Chinese Journal of Applied Chemistry, 2021, 38(12): 0-0.
[5]	WU Qiu-Ping, CAI Kun-Ting, WANG Yuan-Kang, SUN Kai, YANG Jin-Bo, HAN Song-Bai, LIU Yun-Tao. Microwave Absorption Properties of Co/C and Microwave-Heat Conversion Properties of Co/C-Polyurethane Phase Change Composites [J]. Chinese Journal of Applied Chemistry, 2021, 38(12): 1588-1598.
[6]	XIAO Fan,CUI Yuanjing,QIAN Guodong. Metal-Organic Frameworks for Fluorescence Detection Applications [J]. Chinese Journal of Applied Chemistry, 2018, 35(9): 1113-1125.
[7]	YUAN Ting,MENG Ting,LI Shuhua,FAN Louzhen. Recent Development of Electroluminescent Diodes Based on Phosphorescent Materials [J]. Chinese Journal of Applied Chemistry, 2018, 35(8): 871-880.
[8]	YUAN Ning,DU Bingjie,JIA Xiaoxia,YANG Jiangfeng,LI Jinping. Research Progress in Preparation Technology and Application of Bimetal Metal-Organic Frameworks Materials [J]. Chinese Journal of Applied Chemistry, 2018, 35(5): 500-510.
[9]	LIU Kang,MA Dingxuan,SHI Zhan. Application of Metal-Organic Frameworks for Separation of Hydrocarbon Mixtures [J]. Chinese Journal of Applied Chemistry, 2017, 34(9): 1006-1016.
[10]	WANG Yutong, FAN Weidong, XIAO Zhenyu, HUANG Zhaodi, XU Lin, ZHANG Liangliang, XING Lixue, DAI Fangna, SUN Daofeng. Solvent-Dependent Synthesis and Fluorescent Properties of Cu(Ⅱ) Metal-Organic Frameworks [J]. Chinese Journal of Applied Chemistry, 2017, 34(9): 1035-1045.
[11]	Xueyan ZHAO,Shouxin BAO,Xuechao CAI,Xiaoqiu ZHENG,Ruixue ZHAO,Yunhui LI,Maolin PANG. Size and Shape Controlled Growth of Micron or Nano Sized Metal Organic Frameworks [J]. Chinese Journal of Applied Chemistry, 2017, 34(9): 979-995.
[12]	LIU Jingwei,SHI Wei,CHENG Peng. Progress of Metal-Organic Frameworks for Lithium Ion Batteries [J]. Chinese Journal of Applied Chemistry, 2017, 34(9): 996-1005.
[13]	XIE Lefang, XING Rui, WANG Fang, WANG Li. Antibacterial Activities of Six Kinds of Polyoxometalates [J]. Chinese Journal of Applied Chemistry, 2017, 34(6): 700-704.
[14]	WANG Bin, WANG Xiaohong, Li Jiuming, WANG Xiaohui, XIE Lijuan, Duan Limei, LIU Zongrui. Electrochromic Properties of Hybrid Mutilayer Film Based on Pressler Type Polyoxometalate P₅W₃₀, Positive Polyelectrolyte and Graphene Oxide [J]. Chinese Journal of Applied Chemistry, 2017, 34(2): 233-241.
[15]	LI Lili, CHEN Bingnian, DENG Yangyang, XIE Lefang, XING Rui, WANG Li. Inhibitory Effects of Dawson Type Polyoxometalates on Tyrosinase [J]. Chinese Journal of Applied Chemistry, 2017, 34(1): 83-89.