Catalysis at the interface of ruthenium carbene and ruthenium hydride chemistry: Organometallic aspects and applications to organic synthesis

被引:359
作者
Schmidt, B [1 ]
机构
[1] Univ Dortmund, Facbereich Chem, D-44227 Dortmund, Germany
关键词
catalysis; hydride complexes; isomerization; metathesis; ruthenium;
D O I
10.1002/ejoc.200300714
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Soon after the introduction of stable and defined ruthenium precatalysts for olefin metathesis it was discovered that double bond migrations May interfere with the metathesis reaction. This undesired side reaction has been attributed to the formation of ruthenium hydride species from metathesis-active ruthenium carbene species in situ, Over the past few years, several studies have indeed revealed the existence of pathways leading from ruthenium carbene to ruthenium hy-dride complexes. Furthermore, a number of examples have been published recently where typical precatalysts for olefin metathesis were found to promote non-metathesis trans-formations efficiently in preparatively useful yields and se-lectivities, presumably via the in situ formation of ruthenium hydride species. These results open up a pathway to the development of novel catalyzed reaction sequences that combine ruthenium carbene- and ruthenium-hydride-mediated steps. This paper provides an overview of the field and covers organometallic aspects as well as synthetic applications. (C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004).
引用
收藏
页码:1865 / 1880
页数:16
相关论文
共 124 条
  • [61] Enamide-olefin ring-closing metathesis
    Kinderman, SS
    van Maarseveen, JH
    Schoemaker, HE
    Hiemstra, H
    Rutjes, FPJT
    [J]. ORGANIC LETTERS, 2001, 3 (13) : 2045 - 2048
  • [62] Isomerisation of N-allyl-N-arylethanamides catalysed by ruthenium complexes
    Krompiec, S
    Pigulla, M
    Bieg, T
    Szczepankiewicz, W
    Kuznik, N
    Krompiec, M
    Kubicki, M
    [J]. JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2002, 189 (02) : 169 - 185
  • [63] Tandem isomerization/Claisen transformation of allyl homoallyl and diallyl ethers into γ,δ-unsaturated aldehydes with a new three component catalyst Ru3(CO)12/imidazolinium salt/Cs2CO3
    Le Nôtre, J
    Brissieux, L
    Sémeril, D
    Bruneau, C
    Dixneuf, PH
    [J]. CHEMICAL COMMUNICATIONS, 2002, (16) : 1772 - 1773
  • [64] Catalytic hydrogenation of alkenes by the ruthenium-carbene complex HRu(CO)Cl(PCy3)(IMes) (IMes = bis(1,3-(2,4,6-trimethylphenyl)imidazol-2-ylidene)
    Lee, HM
    Smith, DC
    He, ZJ
    Stevens, ED
    Yi, CS
    Nolan, SP
    [J]. ORGANOMETALLICS, 2001, 20 (04) : 794 - 797
  • [65] Leeuwenburgh MA, 1997, SYNLETT, P1263
  • [66] Metathesis of electron-rich olefins: Structure and reactivity of electron-rich carbene complexes
    Louie, J
    Grubbs, RH
    [J]. ORGANOMETALLICS, 2002, 21 (11) : 2153 - 2164
  • [67] Tandem catalysis: The sequential mediation of olefin metathesis, hydrogenation, and hydrogen transfer with single-component Ru complexes
    Louie, J
    Bielawski, CW
    Grubbs, RH
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (45) : 11312 - 11313
  • [68] THE ALCOHOLYSIS OF HYDROSILANES
    LUKEVICS, E
    DZINTARA, M
    [J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1985, 295 (03) : 265 - 315
  • [69] Activation of silanes by Grubbs' carbene complex Cl2(PCy3)2Ru=CHPh:: dehydrogenative condensation of alcohols and hydrosilylation of carbonyls
    Maifeld, SV
    Miller, RL
    Lee, D
    [J]. TETRAHEDRON LETTERS, 2002, 43 (36) : 6363 - 6366
  • [70] Cross-metathesis vs. silylative coupling of vinyl alkyl ethers with vinylsilanes catalyzed by a ruthenium-carbene complex (Grubbs catalyst)
    Marciniec, B
    Kujawa, M
    Pietraszuk, C
    [J]. NEW JOURNAL OF CHEMISTRY, 2000, 24 (09) : 671 - 675