期刊信息
- 刊名： 河北师范大学学报（自然科学版）Journal of Hebei Normal University (Natural Science)
- 主办： 河北师范大学
- ISSN： 1000-5854
- CN： 13-1061/N
- 中国科技核心期刊
- 中国期刊方阵入选期刊
- 中国高校优秀科技期刊
- 华北优秀期刊
- 河北省优秀科技期刊
基于钌配合物催化醇类化合物氧化反应研究进展
- (河北师范大学 化学与材料科学学院,河北 石家庄 050024)
-
DOI：10.13763/j.cnki.jhebnu.nse.202303006
Research Progress on the Oxidation of Alcohols Catalyzed by Ruthenium Complex
摘要/Abstract
摘要：
过渡金属配合物催化醇类化合物氧化成相应的羰基化合物是制备醛酮类化合物的一种重要方法. 钌配合物因其具有多重价态，催化活性高且热稳定性好而备受关注. 近年来，基于钌配合物催化的醇类化合物氧化反应在有机合成中得到了快速发展，并取得了良好的研究结果. 综述了近年来均相钌配合物在环境友好型氧化剂(氧气、过氧化氢等)作用下催化醇类化合物的氧化反应和脱氢反应，介绍了典型的反应机理，进一步展望了其研究前景.
Abstract：
Transition metal complexes-catalyzed oxidation of alcohols to corresponding carbonyl compounds is an important method to prepare aldehydes and ketones. Ruthenium complexes have attracted much attention because of their multiple valence states,high catalytic activity and some thermal stability. In recent years,the oxidation of alcohols catalyzed by ruthenium complexes has developed rapidly in organic synthesis,and some research results have been obtained. The oxidation and dehydrogenation of alcohols catalyzed by homogeneous ruthenium complexes under the action of environment-friendly oxidants(oxygen,hydrogen peroxide,etc. )in recent years were reviewed. The representative mechanisms were introduced,and its research prospet was also prospected.
关键词
Key words：
ruthenium complex
;
oxidation
;
dehydrogenation
;
carbonyl compound
参考文献 22
- [1] GLIN＇SKI M,KIJEN＇SKI J,SITARSKA B. Catalytic Transformations of 1-octanol and 2-ethyl-1-hexanol over Oxide Catalysts,1. Transition Metal Oxides as Catalysts[J]. React Kinet Catal Lett,1997,62(2):377-382. doi:10. 1007/BF02475479
- [2] STEVENS R V,CHAPMAN K T,WELLER H N. Convenient and Inexpensive Procedure for Oxidation of Secondary Alcohols to Ketones[J]. J Org Chem,1980,45(10):2030-2032. doi:10. 1021/jo01298a066
- [3] SHARMA V B,JAIN S L,SAIN B. Cobalt(II) Schiff Base Catalyzed Aerobic Oxidation of Secondary Alcohols to Ketones[J]. J Mol Catal A:Chem,2004,212(1/2):55-59. doi:10. 1016/j. molcata. 2003. 10. 042
- [4] NAJAFPOUR M M,AMINI M,BAGHERZADEH M,et al. Synthesis,Structural Characterization and Alcohol Oxidation Activity of a New Mononuclear Manganese(II) Complex[J]. Transition Met Chem,2010,35(3):297-303. doi:10. 1007/s11243-010-9327-4
- [5] MARKóI E,GILES P R,TSUKAZAKI M,et al. Efficient,Aerobic,Ruthenium-catalyzed Oxidation of Alcohols into Aldehydes and Ketones[J]. J Am Chem Soc,1997,119(51):12661-12662. doi:10. 1021/ja973227b
- [6] ALABAU R G,ESTERUELAS M A,MARTI＇NEZ A,et al. Base-free and Acceptorless Dehydrogenation of Alcohols Catalyzed by an Iridium Complex Stabilized by a N,N,N-osmaligand[J]. Organometallics,2018,37(16):2732-2740. doi:10. 1021/acs. organomet. 8b00380
- [7] RAY R,CHANDRA S,MAITI D,et al. Simple and Efficient Ruthenium-catalyzed Oxidation of Primary Alcohols with Molecular Oxygen[J]. Chem Eur J,2016,22(26):8814-8822. doi:10. 1002/chem. 201601800
- [8] HAN Q,GUO X X,ZHOU X T,et al. Efficient Selective Oxidation of Alcohols to Carbonyl Compounds Catalyzed by Ru-terpyridine Complexes with Molecular Oxygen[J]. Inorg Chem Commun,2020,112:107544. doi:10. 1016/j. inoche. 2019. 107544
- [9] ZHOU X T,JI H B,LIU S G. Solvent-free Selective Oxidation of Primary and Secondary Alcohols Catalyzed by Ruthenium-bis (Benzimidazole) Pyridinedicarboxylate Complex Using Hydrogen Peroxide as an Oxidant[J]. Tetrahedron Lett,2013,54(29):3882-3885. doi:10. 1016/j. tetlet. 2013. 05. 055
- [10] WANG J X,ZHOU X T,HAN Q,et al. Efficient and Selective Oxidation of Alcohols to Carbonyl Compounds at Room Temperature by a Ruthenium Complex Catalyst and Hydrogen Peroxide[J]. New J Chem,2019,43(48):19415-19421. doi:10. 1039/c9nj04393d
- [11] ZHANG Y C,ZHAO L Y,ZHANG H Y,et al. Oxidation of Alkanes and Secondary Alcohols to Ketones with tert-butyl Hydroperoxide Catalyzed by a Water-soluble Ruthenium Complex Under Solvent-free Conditions[J]. Appl Organomet Chem,2017,31(9):e3709. doi:10. 1002/aoc. 3709
- [12] DUTTA M,BANIA K K,PRATIHAR S. Remote ′Imidazole′-based Ruthenium(II) Para-cymene Pre-catalyst for the Selective Oxidation Reaction of Alkyl Arenes and Alcohols[J]. Chem Asian J,2020,15(6):926-932. doi:10. 1002/asia. 201901760
- [13] SINGH P R,MAJI A,SINGH O,et al. Transfer Hydrogenation via Generation of Hydride Intermediate and Base-free Alcohol Oxidation Activity Studies on Designed Ruthenium Complexes Derived from NNN Pincer Type Ligands[J]. Appl Organomet Chem,2020,34(7):e5615. doi:10. 1002/aoc. 5615
- [14] YAN X L,YUE X H,LIU K,et al. Synthesis and Structures of Ruthenium Carbonyl Complexes Bearing Pyridine-alkoxide Ligands and Their Catalytic Activity in Alcohol Oxidation[J]. Front Chem,2019,7:394. doi:10. 3389/fchem. 2019. 00394
- [15] WANG Q F,CHAI H N,YU Z K. Dimeric Ruthenium(II)-NNN Complex Catalysts Bearing a Pyrazolyl-pyridylamino-pyridine Ligand for Transfer Hydrogenation of Ketones and Acceptorless Dehydrogenation of Alcohols[J]. Organometallics,2017,36(18):3638-3644. doi:10. 1021/acs. organomet. 7b00587
- [16] WANG Z,PAN B,LIU Q B,et al. Efficient Acceptorless Dehydrogenation of Secondary Alcohols to Ketones Mediated by a PNN-Ru(II) Catalyst[J]. Catal Sci Technol,2017,7(8):1654-1661. doi:10. 1039/c7cy00342k
- [17] BHATIA A,MUTHAIAH S. Well-defined Ruthenium Complex for Acceptorless Alcohol Dehydrogenation in Aqueous Medium[J]. ChemistrySelect,2018,3(13):3737-3741. doi:10. 1002/slct. 201702981
- [18] WANG Q F,CHAI H N,YU Z K. Acceptorless Dehydrogenation of N-heterocycles and Secondary Alcohols by Ru(II)-NNC Complexes Bearing a Pyrazoyl-indolyl-pyridine Ligand[J]. Organometallics,2018,37(4):584-591. doi:10. 1021/acs. organ-omet. 7b00902
- [19] HAO Z Q,YAN X L,LIU K,et al. Ruthenium Carbonyl Complexes with Pyridine-alkoxide Ligands:Synthesis,Characterization and Catalytic Application in Dehydrogenative Oxidation of Alcohols[J]. New J Chem,2018,42(18):15472-15478. doi:10. 1039/c8nj03706j
- [20] HAO Z Q,LIU K,FENG Q,et al. Ruthenium(II) Complexes Bearing Schiff Base Ligands for Efficient Acceptorless Dehydrogenation of Secondary Alcohols[J]. Chin J Chem,2021,39(1):121-128. doi:10. 1002/cjoc. 202000363
- [21] WANG Q F,DU W M,LIU T T,et al. Ruthenium(II)-NNN Complex Catalyzed Oppenauer-type Oxidation of Secondary Alcohols[J]. Tetrahedron Lett,2014,55(9):1585-1588. doi:10. 1016/j. tetlet. 2014. 01. 072
- [22] DONG Q,MA Z W,HAO Z Q,et al. Preparation of Trinuclear Ruthenium Clusters Based on Piconol Ligands and Their Application in Oppenauer-type Oxidation of Secondary Alcohols[J]. Appl Organomet Chem,2021,35(9):e6336. doi:10. 1002/aoc. 6336