Ruthenium-Indenylidene Complexes: Scope in Cross-Metathesis Transformations

被引:41
作者
Boeda, Fabien [1 ]
Bantreil, Xavier [1 ]
Clavier, Herve [1 ]
Nolan, Steven P. [1 ]
机构
[1] Inst Chem Res Catalonia ICIQ, Tarragona 43007, Spain
关键词
cross-metathesis; indenylidenes; N-heterocyclic carbenes; phosphines; ruthenium;
D O I
10.1002/adsc.200800495
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
A comparative study examining the catalytic activity of a series of five indenylidene-containing ruthenium complexes in olefin cross-metathesis reactions is presented. Results reveal the greater efficiency of precatalyst 5, highlighting the key role of the N,N'-bis(2,6-diisopropylphenyl)imidazol-2-yli-dene (IPr) ligand for this transformation. The scope of this precatalyst was investigated and several microwave experiments were carried out allowing for catalyst loadings as low as 01 mol%. Overall, cross-metathesis products were isolated in moderate to excellent yields with high stereoselectivity.
引用
收藏
页码:2959 / 2966
页数:8
相关论文
共 73 条
[1]   Carboxylates as pronucleophiles in the phosphine-catalyzed γ-addition reaction [J].
Alvarez-Ibarra, C ;
Csáky, AG ;
de la Oliva, CG .
TETRAHEDRON LETTERS, 1999, 40 (48) :8465-8467
[2]  
[Anonymous], [No title captured]
[3]   Reactivity and regiochemical behavior in the solvolysis reactions of (2,2-difluorocyclopropyl)methyl tosylates [J].
Battiste, MA ;
Tian, F ;
Baker, JM ;
Bautista, O ;
Villalobos, J ;
Dolbier, WR .
JOURNAL OF FLUORINE CHEMISTRY, 2003, 119 (01) :39-51
[4]   Advanced fine-tuning of Grubbs/Hoveyda olefin metathesis catalysts: a further step toward an optimum balance between antinomic properties [J].
Bieniek, Michal ;
Bujok, Robert ;
Cabaj, Maciej ;
Lugan, Noel ;
Lavigne, Guy ;
Arlt, Dieter ;
Grela, Karol .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (42) :13652-13653
[5]   Ruthenium-indenylidene complexes: powerful tools for metathesis transformations [J].
Boeda, Fabien ;
Clavier, Herve ;
Nolan, Steven P. .
CHEMICAL COMMUNICATIONS, 2008, (24) :2726-2740
[6]   Phosphabicyclononane-containing Ru complexes: Efficient pre-catalysts for olefin metathesis reactions [J].
Boeda, Fabien ;
Clavier, Herve ;
Jordaan, Margaritha ;
Meyer, Wolfgang H. ;
Nolan, Steven P. .
JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (01) :259-263
[7]   SYNTHESIS OF SOME NEW HIGHLY FUNCTIONALIZED C-6-SYNTHONS [J].
BUSQUE, F ;
DEMARCH, P ;
FIGUEREDO, M ;
FONT, J .
TETRAHEDRON, 1995, 51 (05) :1503-1508
[8]   A general model for selectivity in olefin cross metathesis [J].
Chatterjee, AK ;
Choi, TL ;
Sanders, DP ;
Grubbs, RH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (37) :11360-11370
[9]   ORIGIN OF REGIOSELECTIVITY IN PATERNO-BUCHI REACTIONS OF BENZOQUINONES WITH ALKYLIDENECYCLOALKANES [J].
CIUFOLINI, MA ;
RIVERAFORTIN, MA ;
ZUZUKIN, V ;
WHITMIRE, KH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (04) :1272-1277
[10]   Ionic liquid anchored "Boomerang" catalysts bearing saturated and unsaturated NHCs: Recyclability in biphasic media for cross-metathesis [J].
Clavier, Herve ;
Nolan, Steven P. ;
Mauduit, Marc .
ORGANOMETALLICS, 2008, 27 (10) :2287-2292