Discovery, Applications, and Catalytic Mechanisms of Shvo's Catalyst

被引:370
作者
Conley, Brian L.
Pennington-Boggio, Megan K.
Boz, Emine
Williams, Travis J. [1 ]
机构
[1] Univ So Calif, Loker Hydrocarbon Res Inst, Los Angeles, CA 90089 USA
关键词
HYDROXYCYCLOPENTADIENYL RUTHENIUM HYDRIDE; DYNAMIC KINETIC RESOLUTION; ASYMMETRIC TRANSFER HYDROGENATION; OPPENAUER-TYPE OXIDATION; GRADIENT SPIN-ECHO; X-RAY-STRUCTURE; N-ALKYLATION; AEROBIC OXIDATION; DIFFUSION MEASUREMENTS; SECONDARY ALCOHOLS;
D O I
10.1021/cr9003133
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A scientific review described the discovery, structure, synthetic application, and reactivity mechanisms of Shvo's catalyst and related cyclopentadienone-ligated metal complexes. Shvo's catalyst was an air- and water-stable crystalline solid that was commercially available from several sources. Youval Shvo and a team of researchers introduced this ruthenium catalyst, which utilized noninnocent cyclopentadienone ligands to stabilize the metal in low oxidation states. The dissociated monomeric forms of the catalyst were composed of a ruthenium hydride and a coordinatively unsaturated dicarbonyl species. The first discrete synthesis of the catalyst was a two-step procedure in which monomeric tricarbonyl complex was prepared, isolated, and converted to dimer. The catalyst catalyzed the transfer dehydrogenation of alcohols in the presence of hydrogen acceptors, such as diphenylacetylene, alkenes, and ketones.
引用
收藏
页码:2294 / 2312
页数:19
相关论文
共 121 条
[1]   Investigation of a Possible Solvent Cage Effect in the Reduction of 4-Aminocyclohexanone by a Hydroxycyclopentadienyl Ruthenium Hydride [J].
Aberg, Jenny B. ;
Backvall, Jan-E. .
CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (30) :9169-9174
[2]   Pulsed gradient spin echo (PGSE) diffusion measurements as a tool for the elucidation of a new type of hydrogen-bonded bicapsular aggregate [J].
Alajarín, M ;
Pastor, A ;
Orenes, RA ;
Martínez-Viviente, E ;
Pregosin, PS .
CHEMISTRY-A EUROPEAN JOURNAL, 2006, 12 (03) :877-886
[3]   Ruthenium(II)-catalyzed Oppenauer-type oxidation of secondary alcohols [J].
Almeida, MLS ;
Beller, M ;
Wang, GZ ;
Backvall, JE .
CHEMISTRY-A EUROPEAN JOURNAL, 1996, 2 (12) :1533-1536
[4]   Ruthenium-catalyzed Oppenauer-type oxidation of 3 beta-hydroxy steroids. A highly efficient entry into the steroidal hormones with 4-en-3-one functionality [J].
Almeida, MLS ;
Kocovsky, P ;
Backvall, JE .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (19) :6587-6590
[5]   RUTHENIUM-CATALYZED ISOMERIZATION OF ALLYLIC ALCOHOLS TO SATURATED KETONES [J].
BACKVALL, JE ;
ANDREASSON, U .
TETRAHEDRON LETTERS, 1993, 34 (34) :5459-5462
[6]   Ruthenium-catalyzed synthesis of secondary alkylamines:: Selective alkylation with aliphatic amines [J].
Baehn, Sebastian ;
Hollmann, Dirk ;
Tillack, Annegret ;
Beller, Matthias .
ADVANCED SYNTHESIS & CATALYSIS, 2008, 350 (13) :2099-2103
[7]   A TRANSITION-METAL-BASED METHOD FOR 1,2-DIAMINATION OF ALKENES - SYNTHESIS OF COBALT DINITROSOALKANES FROM ALKENES, NITRIC-OXIDE, AND (ETA-5-CYCLOPENTADIENYL)NITROSYLCOBALT DIMER AND THEIR REDUCTION TO PRIMARY VICINAL DIAMINES [J].
BECKER, PN ;
BERGMAN, RG .
ORGANOMETALLICS, 1983, 2 (07) :787-796
[8]   Oxidative conversion of amines into benzoxazoles using hydrogen transfer catalysis [J].
Blacker, A. John ;
Farah, Mohamed M. ;
Marsden, Stephen P. ;
Saidi, Ourida ;
Williams, Jonathan M. J. .
TETRAHEDRON LETTERS, 2009, 50 (45) :6106-6109
[9]   An efficient method for the selective iridium-catalyzed monoalkylation of (hetero)aromatic amines with primary alcohols [J].
Blank, Benoit ;
Madalska, Martyna ;
Kempe, Rhett .
ADVANCED SYNTHESIS & CATALYSIS, 2008, 350 (05) :749-758
[10]   Application of physical organic methods to the investigation of organometallic reaction mechanisms [J].
Blum, SA ;
Tan, KL ;
Bergman, RG .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (11) :4127-4137