Bis-mixed-carbene ruthenium-thiolate-alkylidene complexes: synthesis and olefin metathesis activity

被引:5
作者
Dahcheh, Fatme [1 ]
Stephan, Douglas W. [1 ]
机构
[1] Univ Toronto, Dept Chem, Toronto, ON M5S 3H6, Canada
关键词
RING-CLOSING METATHESIS; INDENYLIDENE COMPLEXES; NOBEL LECTURE; IN-SITU; CATALYSTS; EFFICIENT; LIGANDS; BEARING; RUCL2(=CHR)(PR(3))(2); POLYMERIZATION;
D O I
10.1039/c4dt03137g
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
A series of bis-carbene Ru-hydride species, including (IMes)(Im(OMe)(2))(PPh3)RuHCl (1) and (SIMes)(Me(2)Im(OMe)(2))(PPh3) RuHCl (2) were prepared and subsequently shown to react with aryl-vinyl-sulfides to give the bis-carbene-alkylidene complexes: Im(OMe)(2)(SIMes)RuCl(SR)(=CHCH3) (R = p-FC6H4 (3), p-(NO2)C6H4 (4)), Im(OMe)(2)(IMes)RuCl(-CHCH3)(SPh) (5), Me(2)Im(OMe)(2)(SIMes)RuCl(-CHCH3)(SPh) (6), Im(OMe)(2)(SIMes)(F5C6S) RuCl(=CHR) (R = C4H9 (9), C5H11 (10)). The activity of these species in the standard Grubbs' tests for ring-opening metathesis polymerization, ring-closing and cross-metathesis are reported. Although these thiolate derivatives are shown to exhibit modest metathesis activities, the reactivity is enhanced in the presence of BCl3.
引用
收藏
页码:1724 / 1733
页数:10
相关论文
共 57 条
[1]   Imidazolylidenes, imidazolinylidenes and imidazolidines [J].
Arduengo, AJ ;
Krafczyk, R ;
Schmutzler, R ;
Craig, HA ;
Goerlich, JR ;
Marshall, WJ ;
Unverzagt, M .
TETRAHEDRON, 1999, 55 (51) :14523-14534
[2]   Ruthenium Complexes Bearing Two N-Heterocyclic Carbene Ligands in Low Catalyst Loading Olefin Metathesis Reactions [J].
Bantreil, Xavier ;
Randall, Rebecca A. M. ;
Slawin, Alexandra M. Z. ;
Nolan, Steven P. .
ORGANOMETALLICS, 2010, 29 (13) :3007-3011
[3]   Reaction between ruthenium(0) complexes and dihalo compounds. A new method for the synthesis of ruthenium olefin metathesis catalysts [J].
Belderrain, TR ;
Grubbs, RH .
ORGANOMETALLICS, 1997, 16 (18) :4001-4003
[4]   Water-promoted regioselective hydrothiolation of alkynes [J].
Bhadra, Sukalyan ;
Ranu, Brindaban C. .
CANADIAN JOURNAL OF CHEMISTRY, 2009, 87 (11) :1605-1609
[5]   Living ring-opening metathesis polymerization [J].
Bielawski, Christopher W. ;
Grubbs, Robert H. .
PROGRESS IN POLYMER SCIENCE, 2007, 32 (01) :1-29
[6]   VINYLCARBENE COMPLEXES OF TITANOCENE [J].
BINGER, P ;
MULLER, P ;
BENN, R ;
MYNOTT, R .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1989, 28 (05) :610-611
[7]   Ruthenium-indenylidene complexes: powerful tools for metathesis transformations [J].
Boeda, Fabien ;
Clavier, Herve ;
Nolan, Steven P. .
CHEMICAL COMMUNICATIONS, 2008, (24) :2726-2740
[8]   Allenylidene-ruthenium complexes as versatile precatalysts for alkene metathesis reactions [J].
Castarlenas, R ;
Fischmeister, C ;
Bruneau, C ;
Dixneuf, PH .
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2004, 213 (01) :31-37
[9]   Highly efficient Ru-pseudohalide catalysts for olefin metathesis [J].
Conrad, JC ;
Parnas, HH ;
Snelgrove, JL ;
Fogg, DE .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (34) :11882-11883
[10]   The first highly active, halide-free ruthenium catalyst for olefin metathesis [J].
Conrad, JC ;
Amoroso, D ;
Czechura, P ;
Yap, GPA ;
Fogg, DE .
ORGANOMETALLICS, 2003, 22 (18) :3634-3636