New palladium(II) complexes with ferrocenyl Schiff bases in the hydrogenation of aromatic ketones

被引:1
作者
Bereta, T. [1 ]
Tylus, W. [2 ]
Trzeciak, A. M. [1 ]
机构
[1] Univ Wroclaw, Fac Chem, 14 F Joliot Curie St, PL-50383 Wroclaw, Poland
[2] Wroclaw Univ Sci & Technol, Fac Chem, Dept Adv Mat Technol, Wybrzeze Wyspianskiego 27 St, PL-50370 Wroclaw, Poland
关键词
Ferrocenyl-imine; Palladium; Hydrogenation; Aromatic ketone; Selectivity; CATALYZED ASYMMETRIC HYDROGENATION; SELECTIVE HYDROGENATION; EFFICIENT ACCESS; NANOPARTICLES; ACETOPHENONE; LIGANDS; ALCOHOLS;
D O I
10.1016/j.poly.2022.116075
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Two new palladium complexes with chelating phosphorus-free ferrocenyl-imine ligands derived from 1,2-diami-nocyclohexane and 1,2-diphenylethylenediamine were investigated in the hydrogenation of aromatic ketones. It was found that these catalysts are active in reactions performed with H2 as well as in transfer hydrogenation using 2-propanol/NaOH as a hydrogen donor. In the hydrogenation of acetophenone (APh), two products could be formed, 1-phenylethanol (PhE) and ethylbenzene (EtB), and the reaction selectivity in the studied system was controlled by the kind of solvent and the amount of free ligand excess. In the hydrogenation of acetophenone derivatives, higher selectivity to 1-arylethanol was achieved under hydrogen transfer conditions than under 10 bars of H2 and some ketones were hydrogenated only using this method.
引用
收藏
页数:7
相关论文
共 50 条
[41]   Highly Selective Hydrogenation of Aromatic Ketones and Phenols Enabled by Cyclic (Amino)(alkyl)carbene Rhodium Complexes [J].
Wei, Yu ;
Rao, Bin ;
Cong, Xuefeng ;
Zeng, Xiaoming .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (29) :9250-9253
[42]   Preparation of a series of Ru(II) complexes with N-heterocyclic carbene ligands for the catalytic transfer hydrogenation of aromatic ketones [J].
Gurbuz, Nevin ;
Ozcan, Emine Ozge ;
Ozdemir, Ismail ;
Cetinkaya, Bekir ;
Sahin, Onur ;
Buyukgungor, Orhan .
DALTON TRANSACTIONS, 2012, 41 (08) :2330-2339
[43]   New iminophosphine-Ru(II) complexes and their application in hydrogenation and transfer hydrogenation [J].
Keles, Mustafa ;
Sahinoglu, Coskun ;
Emir, Duygu M. ;
Mart, Mehmet .
APPLIED ORGANOMETALLIC CHEMISTRY, 2014, 28 (10) :768-772
[44]   Comparative Study of Homogeneous and Silica Immobilized N N and N O Palladium(II) Complexes as Catalysts for Hydrogenation of Alkenes, Alkynes and Functionalized Benzenes [J].
Akiri, Saphan O. ;
Ngcobo, Nondumiso L. ;
Ojwach, Stephen O. .
CATALYSIS LETTERS, 2020, 150 (10) :2850-2862
[45]   Two pseudo-N3 ligands and the catalytic activity of their ruthenium(II) complexes in transfer hydrogenation and hydrogenation of ketones [J].
Yu, Z. K. ;
Zeng, F. L. ;
Sun, X. J. ;
Deng, H. X. ;
Dong, J. H. ;
Chen, J. Z. ;
Wang, H. M. ;
Pei, C. X. .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2007, 692 (11) :2306-2313
[46]   Synthesis, Characterization, and Antibacterial Activity of Nickel(II) Complexes With Schiff Bases [J].
Xiong, Yan .
SYNTHESIS AND REACTIVITY IN INORGANIC METAL-ORGANIC AND NANO-METAL CHEMISTRY, 2013, 43 (08) :961-965
[47]   Iron(II) Complexes for the Efficient Catalytic Asymmetric Transfer Hydrogenation of Ketones [J].
Meyer, Nils ;
Lough, Alan J. ;
Morris, Robert H. .
CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (22) :5605-5610
[48]   Pd(II)-NNN Pincer Complexes for Catalyzing Transfer Hydrogenation of Ketones [J].
Jerome, Peter ;
Haribabu, Jebiti ;
Bhuvanesh, Nattamai S. P. ;
Karvembu, Ramasamy .
CHEMISTRYSELECT, 2020, 5 (43) :13591-13597
[49]   Catalytic activity of palladium(II) complexes with tridentate nitrogen ligands in the hydrogenation of alkenes and alkynes [J].
Costa, M ;
Pelagatti, P ;
Pelizzi, C ;
Rogolino, D .
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2002, 178 (1-2) :21-26
[50]   Novel binuclear palladium(II) complexes of 2-oxoquinoline-3-carbaldehyde Schiff bases: Synthesis, structure and catalytic applications [J].
Priyarega, Sivakumar ;
Raja, Duraisamy Senthil ;
Babu, Sundaram Ganesh ;
Karvembu, Ramasamy ;
Hashimoto, Takeshi ;
Endo, Akira ;
Natarajan, Karuppannan .
POLYHEDRON, 2012, 34 (01) :143-148