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PLATINUM METALS REVIEW a Quarterly Survey of Research on the Platinum Metals and of Developments in Their Application in Industry

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PLATINUM METALS REVIEW a Quarterly Survey of Research on the Platinum Metals and of Developments in Their Application in Industry E-ISSN 1471–0676 PLATINUM METALS REVIEW A Quarterly Survey of Research on the Platinum Metals and of Developments in their Application in Industry www.platinummetalsreview.com VOL. 48 OCTOBER 2004 NO. 4 Contents Ruthenium Vinylidene Complexes 148 By Valerian Dragutan and Ileana Dragutan 13th International Congress on Catalysis 154 A conference review by Alvaro Amieiro-Fonseca, Janet M. Fisher and Sonia Garcia Oxidation States of Ruthenium and Osmium 157 A book review by C. F. J. Barnard and S. C. Bennett Iridium-Based Hexacyanometallate Thin Films 159 in Aqueous Electrolytes By Kasem K. Kasem and Leslie Huddleston Increased Luminescent Lifetimes of Ru(II) Complexes 168 Carbon Nanotube Particulates in Electron Emitters 168 Palladium-Iron Dispersed in Carbon 168 Catalysis by Gold/Platinum Group Metals 169 By David T. Thompson The Discoverers of the Osmium Isotopes 173 By J. W. Arblaster Fundamentals of Kinetics and Catalysis 180 A book review by Tim Watling Bicentenary of Four Platinum Group Metals 182 By W. P. Griffith Abstracts 190 New Patents 193 Indexes to Volume 48 195 Communications should be addressed to: The Editor, Susan V. Ashton, Platinum Metals Review, [email protected] Johnson Matthey Public Limited Company, Hatton Garden, London EC1N 8EE DOI: 10.1595/147106704X4835 Ruthenium Vinylidene Complexes SYNTHESES AND APPLICATIONS IN METATHESIS CATALYSIS By Valerian Dragutan* and Ileana Dragutan Institute of Organic Chemistry, Romanian Academy, 202B Spl. Independentei, PO Box 15-254, 060023 Bucharest, Romania; *E-mail: [email protected] This paper surveys an attractive family of ruthenium complexes with great potential for applications in organic and polymer synthesis. When compared with traditional ruthenium alkylidene pre-catalysts, these alternative ruthenium vinylidene complexes are easily accessible from commercial starting materials. In addition, they display moderate to high metathesis activity and stability, and exhibit good tolerance towards an array of functional groups, air and moisture. Their synthesis, physical-chemical properties and catalytic attributes indicate they are quite promising initiators of efficient applications in ring-closing metathesis, cross metathesis and ring-opening metathesis polymerisation. Previous papers recently published in this These ruthenium complexes enjoyed consider- Journal have highlighted the role and scope of plat- able popularity within the organic synthesis inum group metals in the development of community, especially the neutral 16-electron metathesis catalysts (1, 2). Following the seminal ruthenium bisphosphane benzylidene complex 3, discovery of the highly active and stereoselective which combines good activity with high tolerance tungsten and molybdenum imido alkylidene towards many organic functionalities, air and mois- metathesis catalysts, for example, 1 and 2 (R = ture. Many improvements in the preparation of classical Grubbs’ catalysts have subsequently been performed (7, 8) and different variations of the lig- and sphere of complex 3 have been created. These Me HC Me HC 2 CHMe2 2 CHMe2 N N include: Schiff base ligated complexes 5 (9–11), N- heterocyclic carbene complexes 6 and 7 (12–14), RO W Me Mo Me Me RO Me and isopropoxy tethered benzylidene complexes 8 RO RO Ph Ph (15). However, their synthesis via hazardous dia- 12 R' N N N Mes Mes alkyl groups) by Schrock and coworkers (3, 4), an Cl ORu Ru important class of ruthenium bisphosphane alkyli- Cl Ph Cl Ph PCy3 dene catalysts, for example, 3 and 4, have been PR3 56 PR Cl 3 Ph PR3 R' Cl PR Ru Ru R' Cl 3 Cl Cl N N H Mes Mes Ru PR3 PR3 Cl Cl Ru Ph 34 Cl O PCy3 R = phenyl (Ph), isopropyl (iPr) or cyclohexyl (Cy) R' = phenyl (Ph) or tert-butyl (tBu) groups 78 R = phenyl (Ph), isopropyl (iPr) or cyclohexyl (Cy) disclosed and successfully applied in metathesis R' = phenyl (Ph) or tert-butyl (tBu) groups reactions by Grubbs and coworkers (5, 6). Mes = mesityl Platinum Metals Rev., 2004, 48, (4), 148–153 148 22 eq.eq PR 3 PR3 H R' Cl H 1/2 Ru _ Ru C C (i) - p-cymene Cl Cl Cl 2 R' PR3 910 zoalkane derivatives remains of considerable con- cymene)]2, see Equation (i). Unfortunately, these cern. complexes showed only moderate metathesis In order to circumvent this important drawback activity in processes such as RCM of unsubstituted of ruthenium benzylidene complexes, research has α,ω-dienes and ROMP of highly strained nor- been directed to produce alternative metathesis ini- bornenes (19). tiators of comparable performance but easier New cationic 18-electron ruthenium vinylidene accessibility from commercial ruthenium sources complexes, for example, 11, 12 and 13, were (16, 17). The present paper reviews the class of designed, prepared and screened for their metathe- ruthenium vinylidene complexes applied as effi- sis activity by Grubbs and coworkers (20) but their cient pre-catalysts in olefin metathesis reactions, applicability remained limited to a small range of such as cross metathesis (CM), ring-closing olefinic substrates. metathesis (RCM) and ring-opening metathesis More effective neutral and cationic 16- and 18- polymerisation (ROMP). electron ruthenium tridentate complexes, for example, 14, 15 and 16, were easily synthesised by Ruthenium Vinylidene Complexes: van Koten and coworkers (21) by treating the Syntheses and Catalytic Properties ruthenium complex [RuCl2(NN'N )(PPh3)] (where A first set of neutral 16-electron ruthenium NN'N is 2,6-bis[(dimethylamino)methyl]pyridine vinylidene complexes 10 was easily prepared by ligand) with 2 equivalents of Ag[BF4], in CH2Cl2, in Katayama and Ozawa (18) from common terminal the presence of an excess of phenylacetylene (iso- alkynes and the arene ruthenium dimer 9, [RuCl2(p- lated yield 95%), see Equation (ii). HB N N N Ph N N N Ph Ph Ru C C PF6 Ru C C PF6 Ru C C PF6 Cl PCy3 Cl PCy 3 Cl PCy3 11 12 13 Ph H Ph H Ph H C C C C NMe C C N 2 NMe NMe Ru N 2 PF6 N 2 PF6 Ru Ru N Cl Me Cl N PPh3 N PPh3 2 Me2 Cl Me2 OTf 14 15 16 Platinum Metals Rev., 2004, 48, (4) 149 2 Ph H C Ph N NMe N C 2 NMe2 2 BF Ru 4 (ii) Cl 2 eq.eq Ag[BF ] Ru Me N 4 2 PPh Me2 N PPh3 Cl 3 CH2Cl2,, 95% 16a Significantly, a highly active and selective, coor- dene complexes coordinated with an imidazolyli- dinatively unsaturated, ruthenium 16-electron dene ligand (22). This class of ruthenium dicationic complex, 16a, was found to quantitative- complexes, including complexes with formula 17 ly promote ROMP of norbornene to [IMes = 1,3-(2',4',6'-trimethylphenyl)imidazol-2- polynorbornene under mild conditions, in the ylidene, R = Cy, R' = tBu] and 18 (iPrIM = absence of any cocatalyst (Scheme I). The IR, 1H 1,3-diisopropyl-4,5-dimethylimidazol-2-ylidene, R' and 13C{1H} NMR spectra of the polynorbornene = Ph) has been prepared directly from the bispho- obtained under the above conditions indicated sphane ruthenium complex 10 (R = Cy) and free 90–95% trans C=C, in accordance with similar imidazoline carbenes or their salts (Scheme II). results reported previously (12). Of these two complexes, 17 and 18, the ruthe- Substantial progress was made by Louie and nium compound 17, possessing a mixed ligand Grubbs through the synthesis of ruthenium vinyli- system, displayed a substantial metathesis activity CC22HH4Cl4Cl2,2 80ºC,,80°C,1h 1h YieldYield 100% 100% 2n n Ph H 2 C C N NMe2 Ru Me2 N PPh3 16a Scheme I IMes Cl H IMes Ru C C Cl R' PR3 PR3 Cl H 17 17 Ru C C Cl R' PR3 iPrIM 22 eq eq. iPrIM 10 Cl H 9 Ru C C Cl R' iPrIM 18 18 Scheme II Platinum Metals Rev., 2004, 48, (4) 150 EtO2C CO Et 2 17 CO2Et (iii) Yield 86% CO2Et IMes IMes H tBu Cl H 1/2 Cl Ru Ru C C (iv) Cl - p-cymene Ru Cl IMes Cl tBu Cl 2 92019 IMes IMes Cl H H Cl H H Ru C C H2C C Ru CH2 C CC (v) Cl tBu R Cl R tBu 19 21 EtO2C CO Et 2 19 CO2Et (vi) Yield 95-96% CO2Et 19 2 (vii) Yield 93% 19 n/2 (viii) Yield 95% n in RCM of diethyl diallylmalonate to substituted proved to be superior to that of the ruthenium cycloolefin (Equation (iii)), although the reaction complex 17, supporting the concept of a higher rate was slower than that with the parent bisimida- degree of unsaturation in the coordination sphere zolylidene ruthenium carbene complex. of the metal promoting catalysis. The pathway for Detailed mechanistic investigations of the generation of the true catalyst 21 from the catalyst ruthenium-catalysed metathesis chemistry strongly precursor 19, by reaction with an olefin substrate, indicated that increased ligand dissociation (that is can be seen in Equation (v). of phosphane) is necessary to accelerate initiation The particular catalytic behaviour of the pre- and thereby enhance catalytic activity in this type catalyst 19 in the RCM of diethyl diallylmalonate, of reaction. Thus, a phosphane-free coordinatively metathesis homodimerisation CM of allyl benzene unsaturated ruthenium vinylidene complex 19 can and ROMP of 1,5-cyclooctadiene is compared in be formed directly in situ from the commercial Equations (vi), (vii) and (viii). It is worth noting ruthenium dimer 9, N-heterocyclic carbene (IMes) that the solvent (hexane or tetrahydrofuran) plays as such or as its salts, and a terminal alkyne an important role in the in situ generation of the (Equation (iv)). ruthenium catalyst from these starting materials. Indeed, the catalytic activity of complex 19 Another interesting array of ruthenium vinyli- Platinum Metals Rev., 2004, 48, (4) 151 Me Br Me Br 1. TlOEt, THF/RT R R N N Me PCy3 H Me 2.
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