Latent ruthenium-indenylidene catalysts bearing a N-heterocyclic carbene and a bidentate picolinate ligand

被引:9
作者
Schmid, Thibault E. [1 ]
Modicom, Florian [1 ]
Dumas, Adrien [1 ]
Borre, Etienne [1 ]
Toupet, Loic [2 ]
Basle, Olivier [1 ]
Mauduit, Marc [1 ]
机构
[1] Ecole Natl Super Chim Rennes, UMR CNRS 6226, F-35708 Rennes 7, France
[2] Univ Rennes 1, Inst Phys Rennes, CNRS, UMR 6251, Rennes, France
来源
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY | 2015年 / 11卷
关键词
latent catalyst; olefin metathesis; picolinate ligand; ruthenium indenylidene; OLEFIN METATHESIS CATALYSTS; COMPLEXES; NHC; POLYMERIZATION; PHOSPHINE;
D O I
10.3762/bjoc.11.169
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A silver-free methodology was developed for the synthesis of unprecedented N-heterocyclic carbene ruthenium indenylidene complexes bearing a bidentate picolinate ligand. The highly stable (SIPr)(picolinate) RuCl(indenylidene) complex 4a (SIPr = 1,3-bis( 2-6-diisopropylphenyl)imidazolidin-2-ylidene) demonstrated excellent latent behaviour in ring closing metathesis (RCM) reaction and could be activated in the presence of a Bronsted acid. The versatility of the catalyst 4a was subsequently demonstrated in RCM, cross-metathesis (CM) and enyne metathesis reactions.
引用
收藏
页码:1541 / 1546
页数:6
相关论文
共 32 条
  • [1] Synthesis and characterization of new ruthenium-based olefin metathesis catalysts coordinated with bidentate Schiff-base ligands
    Chang, S
    Jones, L
    Wang, CM
    Henling, LM
    Grubbs, RH
    [J]. ORGANOMETALLICS, 1998, 17 (16) : 3460 - 3465
  • [2] N-heterocyclic carbene and phosphine ruthenium indenylidene precatalysts: A comparative study in Olefin metathesis
    Clavier, Herve
    Nolan, Steven P.
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2007, 13 (28) : 8029 - 8036
  • [3] Indenylidene Ruthenium Complex Bearing a Sterically Demanding NHC Ligand: An Efficient Catalyst for Olefin Metathesis at Room Temperature
    Clavier, Herve
    Urbina-Blanco, Cesar A.
    Nolan, Steven P.
    [J]. ORGANOMETALLICS, 2009, 28 (09) : 2848 - 2854
  • [4] Towards Long-Living Metathesis Catalysts by Tuning the N-Heterocyclic Carbene (NHC) Ligand on Trifluoroacetamide-Activated Boomerang Ru Complexes
    Clavier, Herve
    Caijo, Frederic
    Borre, Etienne
    Rix, Diane
    Boeda, Fabien
    Nolan, Steven P.
    Mauduit, Marc
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2009, 2009 (25) : 4254 - 4265
  • [5] Synthesis and evaluation of a new class of ruthenium-based catalytic systems for atom transfer radical addition and enol ester synthesis
    De Clercq, B
    Verpoort, F
    [J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2003, 672 (1-2) : 11 - 16
  • [6] Activity of a new class of ruthenium based ring-closing metathesis and ring-opening metathesis polymerization catalysts coordinated with a 1,3-dimesityl-4,5-dihydroimidazol-2-ylidene and a Schiff base ligand
    De Clercq, B
    Verpoort, F
    [J]. TETRAHEDRON LETTERS, 2002, 43 (50) : 9101 - 9104
  • [7] Denk K, 2002, ADV SYNTH CATAL, V344, P666, DOI 10.1002/1615-4169(200208)344:6/7<666::AID-ADSC666>3.0.CO
  • [8] 2-0
  • [9] Latent Olefin Metathesis Catalysts for Polymerization of Dcpd
    Drozdzak, Renata
    Nishioka, Naoki
    Recher, Gilles
    Verpoort, Francis
    [J]. OLEFIN METATHESIS, 2010, 293 : 1 - +
  • [10] A dormant ruthenium catalyst bearing a chelating carboxylate ligand: In situ activation and application in metathesis reactions
    Gawin, Rafal
    Makal, Anna
    Wozniak, Krzysztof
    Mauduit, Marc
    Grela, Karol
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (38) : 7206 - 7209