Catalytic activity and selectivity of a range of ruthenium complexes tested in the styrene/EDA reaction system

被引:4
作者
Ding, Fu [1 ]
Sun, Ya-guang [1 ]
Verpoort, Francis [2 ,3 ]
Dragutan, Valerian [4 ]
Dragutan, Ileana [4 ]
机构
[1] Shenyang Univ Chem Technol, Lab Coordinat Chem, Shenyang 110142, Peoples R China
[2] Wuhan Univ Technol, Fac Sci, Dept Chem,Ctr Chem & Mat Engn, State Key Lab Adv Technol Mat Synth & Proc, Wuhan 430070, Peoples R China
[3] Univ Ghent, Dept Inorgan & Phys Chem, B-9000 Ghent, Belgium
[4] Romanian Acad, Inst Organ Chem, Bucharest 060023, Romania
关键词
Cyclopropanation; N-heterocyclic carbenes; Schiff bases; Ruthenium complexes; C-C coupling; SCHIFF-BASE LIGANDS; N-HETEROCYCLIC CARBENES; OLEFIN METATHESIS; CYCLOPROPANATION REACTIONS; ENANTIOSELECTIVE SYNTHESIS; ORGANIC-SYNTHESIS; CROSS-METATHESIS; POLYMERIZATION; DIAZOACETATES; PRECURSORS;
D O I
10.1016/j.molcata.2014.02.009
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
The complex ensemble of competing chemical processes (cyclopropanation, metathesis, dimerisation) involved in the reaction of ethyl diazoacetate with styrene is examined in the presence of a panel of ten ruthenium complexes. Our results, focusing on the catalysts' activity and selectivity, showcased the new NHC-containing complex 10 and the Fischer carbene 7 as leading to best chemoselectivities for cyclopropanation while the bidentate Schiff-base complexes 3 and 4 provided highest stereoselectivity. The traditionally metathesis-active Grubbs I catalyst (5) could be manipulated, by working under high dilution, to display moderate activity in cyclopropanation whereas the Grubbs II catalyst (6) totally promoted metathesis. Data obtained with the above set of Ru complexes strongly support the premise that ligand structure and configuration in the Ru coordination sphere are essential factors in controlling the reaction pathways. (C) 2014 Elsevier B.V. All rights reserved.
引用
收藏
页码:86 / 94
页数:9
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