N,N'-dialkyl- and N-alkyl-N-mesityl-substituted N-heterocyclic carbenes as ligands in Grubbs catalysts

被引:81
作者
Ledoux, Nele [1 ]
Allaert, Bart [1 ]
Pattyn, Siegfried [1 ]
Vander Mierde, Hans [1 ]
Vercaemst, Carl [1 ]
Verpoort, Francis [1 ]
机构
[1] Univ Ghent, Dept Inorgan & Phys Chem, Lab Organomet Chem & Catalysis, B-9000 Ghent, Belgium
关键词
carbene ligands; metathesis; ruthenium;
D O I
10.1002/chem.200600064
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Various symmetrically and asymmetrically substituted N-heterocyclic carbene (NHC) ligands bearing aliphatic nitrogen-containing side groups have been synthesised. In our attempts to isolate the corresponding second-generation Grubbs catalysts, we were unsuccessful when using the symmetrical aliphatic NEC ligands. For the asymmetrical ligands bearing an aliphatic moiety on one side and an aromatic mesityl group on the other side, substitution of a phosphine ligand was achieved. The performance of a soformed series of Ru-based metathesis initiators has been evaluated for the ring-opening metathesis polymerisation (ROMP) of cycloocta-1,5-diene and the ring-closing metathesis (RCM) of diethyl diallylmalonate.
引用
收藏
页码:4654 / 4661
页数:8
相关论文
共 44 条
[1]   Mechanism and activity of ruthenium olefin metathesis catalysts: The role of ligands and substrates from a theoretical perspective [J].
Adlhart, C ;
Chen, P .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (11) :3496-3510
[2]  
Bielawski C.W., 2000, ANGEW CHEM, P112
[3]  
Bielawski CW, 2000, ANGEW CHEM INT EDIT, V39, P2903, DOI 10.1002/1521-3773(20000818)39:16<2903::AID-ANIE2903>3.0.CO
[4]  
2-Q
[5]   Steric and electronic effects in the bonding of N-heterocyclic ligands to transition metals [J].
Cavallo, L ;
Correa, A ;
Costabile, C ;
Jacobsen, H .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2005, 690 (24-25) :5407-5413
[6]   New bidentate alkoxy-NHC ligands for enantioselective copper-catalysed conjugate addition [J].
Clavier, H ;
Coutable, L ;
Guillemin, JC ;
Mauduit, M .
TETRAHEDRON-ASYMMETRY, 2005, 16 (05) :921-924
[7]   The first metal complexes of bis(diisopropylamino)carbene: synthesis, structure and ligand properties [J].
Denk, K ;
Sirsch, P ;
Herrmann, WA .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2002, 649 (02) :219-224
[8]   Adamantyl-substituted N-heterocyclic carbene ligands in second-generation Grubbs-type metathesis catalysts [J].
Dinger, MB ;
Nieczypor, P ;
Mol, JC .
ORGANOMETALLICS, 2003, 22 (25) :5291-5296
[9]  
Dinger MB, 2002, ADV SYNTH CATAL, V344, P671, DOI 10.1002/1615-4169(200208)344:6/7<671::AID-ADSC671>3.0.CO
[10]  
2-G