Organometallic chemistry volume 36 specialist periodical reports

Organometallic Chemistry Volume 36 A Specialist Periodical Report Organometallic Chemistry Volume 36 A Review of the Literature Published between January 2007 and December 2008 Editors I Fairlamb and J Lynam, University of York, UK Authors J.G Brennan, State University of New Jersey, USA T.H Bullock, University of Cambridge, UK M.P Cifuentes, Australian National University, Canberra, Australia V Engels, University of Cambridge, UK M.G Humphrey, Australian National University, Canberra, Australia D.L Kays, University of Nottingham, UK S.T Liddle, University of Nottingham, UK R.L Melen, University of Cambridge, UK D.P Mills, University of Nottingham, UK B.E Moulton, Manchester, UK N.J Patmore, University of Sheffield, UK A Sella, University College London, Uk A.E.H Wheatley, University of Cambridge, UK A.J Wooles, University of Nottingham, UK C.E Willans, University of Leeds, UK D.S Wright, University of Cambridge, UK If you buy this title on standing order, you will be given FREE access to the chapters online Please contact sales@rsc.org with proof of purchase to arrange access to be set up Thank you ISBN 978-1-84755-950-0 ISSN 0301-0074 DOI 10.1039/9781847559616 A catalogue record for this book is available from the British Library & The Royal Society of Chemistry 2010 All rights reserved Apart from fair dealing for the purposes of research or private study for non-commercial purposes, or for private study, criticism or review, as permitted under the Copyright, Designs and Patents Act, 1988 and the Copyright and Related Rights Regulations 2003, this publication may not be reproduced, stored or transmitted, in any form or by any means, without the prior permission in writing of The Royal Society of Chemistry, or in the case of reproduction in accordance with the terms of the licences issued by the Copyright Licensing Agency in the UK, or in accordance with the terms of the licences issued by the appropriate Reproduction Rights Organization outside the UK Enquiries concerning reproduction outside the terms stated here should be sent to The Royal Society of Chemistry at the address printed on this page Published by The Royal Society of Chemistry, Thomas Graham House, Science Park, Milton Road, Cambridge CB4 0WF, UK Registered Charity Number 207890 For further information see our web site at www.rsc.org Preface Ian J S Fairlamba and Jason M Lynama DOI: 10.1039/9781847559616-FP005 The format for this Volume follows on from the modifications made to the structure of this journal series, which were introduced in Volumes 34 and 35 The Volume is split into two sections: critical reviews and comprehensive reviews A series of critical reviews and perspectives which focus on specific aspects of organometallic chemistry, which interface with other fields of study, are provided For this Volume, the critical reviews examine the role played by new ligands motifs for example Charlotte Willans (University of Leeds, UK) highlights the cutting-edge applications of N-heterocyclic carbenes in non-transition metal chemistry This is coupled with an exciting and comprehensive review of bis(phosphorus-stabilised)methanide and methandiide derivatives ligands in early transition metals and f-elements by Stephen Liddle, David Mills and Ashley Wooles (University of Nottingham, UK) The use of bulky terphenyl ligand systems in stabilising low valent metal complexes has been elegantly described by Deborah Kays (University of Nottingham, UK), and the chemistry multiply bonded paddlewheel compounds with potential applications in molecular electronic devices has been reviewed by Nathan Patmore (University of Sheffield, UK) For the first time in this series, structural, synthetic and mechanistic aspects pertaining to the versatile and widely used Pauson-Khand reaction of alkynes, alkenes and dicobalt(0) octacarbonyl is examined by Benjamin Moulton (Reaxa Ltd., Manchester, UK) Comprehensive reviews of the organometallic chemistry of a wide range of elements from across the periodic table are included in this Volume These articles cover the literature from 2006 and 2007 Significant contributions are made by John Brennan and Andrea Sella (covering the f-elements) Volker Engels and Andrew Wheatley have reviewed recent developments in alkali and coinage metals with a focus on organolithium and organocuprate chemistry Thomas Bullock, Rebecca Melen and Dominic Wright discuss the key aspects in Group (Be-Ba) and Group 12 (Zn-Hg) compounds Mark Humphrey and Marie Cifuentes discuss a selection of highlights on metal cluster chemistry In summary, this volume covers a wide range of organometallic chemistry aligned with important applications in other key areas We have tried to ensure that a broad spectrum of topics which illustrate the diverse nature of modern organometallic chemistry are included in this Specialist Periodical Report a Department of Chemistry, University of York, York YO51 5DD, UK Organomet Chem., 2010, 36, v–v | v  c The Royal Society of Chemistry 2010 CONTENTS Cover Ball and stick representation of Grubbs generation II catalyst Preface Ian J S Fairlamb and Jason M Lynam v Non-transition metal N-heterocyclic carbene complexes Charlotte E Willans Introduction s-Block-carbenes p-Block-carbenes f-Element-carbenes Conclusion References Bis(phosphorus-stabilised)methanide and methandiide derivatives of group 1–5 and f-element metals Stephen T Liddle, David P Mills and Ashley J Wooles Introduction Methane syntheses Group methanides and methandiides 1 21 25 26 29 29 30 31 Organomet Chem., 2010, 36, vii–x | vii  c The Royal Society of Chemistry 2010 Group methanides and methandiides Group and f-element methanides and methandiides Group methanides and methandiides Group methanides and methandiides Conclusions References 35 38 47 51 53 53 The stabilisation of organometallic complexes using m-terphenyl ligands 56 Deborah L Kays Introduction Ligands Complexes of Complexes of Complexes of Complexes of Complexes of Complexes of Conclusions References group groups and groups 6-9 group 10 group 11 group 12 Recent developments in the chemistry of metal-metal multiply bonded paddlewheel compounds Nathan J Patmore Introduction Chromium Molybdenum and tungsten Rhenium complexes Diruthenium complexes Dirhodium complexes Conclusions References The Pauson-Khand reaction Benjamin E Moulton Introduction References viii | Organomet Chem., 2010, 36, vii–x 56 56 57 59 59 66 67 70 72 72 77 77 78 78 81 82 85 90 90 93 93 118 121 Scandium, Yttrium and the Lanthanides John G Brennan and Andrea Sella Introduction Hydrocarbyl chemical reactivity Redox chemistry Catalysis Organolanthanides in organic synthesis Organolanthanides in materials synthesis Polymer chemistry Synthesis and characterization of new compounds Theory 10 Spectroscopy/electronic structure Acknowledgements Abbreviation References 121 121 129 130 132 133 133 136 141 142 143 143 144 Alkali/coinage metals – organolithium, organocuprate chemistry 148 Volker Engels and Andrew E H Wheatley The alkali metals Group II Abbreviations References 148 153 161 162 168 Group (Be-Ba) and group 12 (Zn-Hg) Thomas H Bullock, Rebecca L Melen and Dominic S Wright Scope and organisation of the review Group Group 12 References 168 168 173 177 Organo-transition metal cluster complexes 182 Mark G 182 182 182 182 183 184 Humphrey and Marie P Cifuentes Introduction Reviews Theory Spectroscopy High-nuclearity clusters Group Organomet Chem., 2010, 36, vii–x | ix Group 8 Group 9 Group 10 10 Group 11 11 Mixed-metal clusters Abbreviations References x | Organomet Chem., 2010, 36, vii–x 184 194 195 196 196 202 203 in 1,2-dichloroethane affords 47, which takes up hydrogen to give the trihydride cluster 48, or reacts with PR3 (R=Ph, Me) to give the monophosphine substituted 47 Further reaction of 47 (L=CO, L =PMe3) with trimethylphosphine results in Ru–Ru bond opening to give 49, which readily loses CO to reform the triangular metal structure 50 The facecapping P(Ph)CQC(PPh2)C(O)CH2C(O) ligand thus functions as a 7- or 9-electron donor ligand in these complexes.35 Thermolysis of Ru3(m-dppm)(CO)9{P(C4H3E)3} (E=S, O) in the presence of Me3NO results in C–H and C–P bond activation to give 51 (L=CO) as an isomeric mixture containing m3-Z2- thiophyne and furyne ligands, respectively Thermolysis of 51 (L=CO, E=S) at 80 1C results in ring-opening of the thiophyne ligand to give the open triruthenium complex 52, containing a m3Z2-1-thia-1,3-butadiene ligand, whereas a similar reaction with the furyne analogue affords the phosphinidene cluster 53 Triphenylphosphine addition to 51 (L=CO) affords 51 (L=PPh3) and reaction with HBr gives 54, with terminal and bridging bromine atoms and an unusual unsymmetric m3-alkynyl ligand with one carbon acting as a bridging alkylidene and the other as a terminally bound Fischer carbene, suggesting the presence of a C–C single bond.36 192 | Organomet Chem., 2010, 36, 182–205 The phosphine thiol HPPhCH2CH2SH reacts with Ru3(m-dppm)(CO)10 to give the chelated product Ru3(m-H)(m-Z2-SCH2CH2PPhH)(m-dppm)(CO)7 and the linked cluster Ru3(m-H)(m-dppm)(CO)8(m-Z2-SCH2CH2PPhH)Ru3(m-dppm) (CO)9, whereas a similar reaction with Ru3(CO)12 affords the tetranuclear cluster 55 Ru3(m-dppm)(CO)10 reacts with HPMe{C6H4(CH2OMe)} to give 56 and 57, the latter resulting from the presence of some adventitious phosphine oxide.37 Reaction of [Os2(m-H)5Cp*2] ỵ with H5OsCp* aords the triangular cluster cation [{OsCp*}3(m-H)6] ỵ , which converts to {OsCp*}3(m3-H)3(mH)2 on treatment with n-butyllithium.38 Reaction of the unsaturated triosmium clusters 58 with ButNC results in C–H bond activation to give 59, whereas similar treatment with 60 (L=CO) leaves the cluster bonding intact giving the substituted product 60 (L=CNBut).39 The multifunctional ligand {Ph2P(2-C6H4)CH=NCH2CH2}3N reacts with three equivalents of Os3(CO)10(NCMe)2, affording a ‘‘triple cluster’’ and then 61 via C–H and C–N bond activation; the ligand acts as a electron donor.40 Os3(m-H) (m-OH)(CO)10 and Os3(CO)10(NCMe)2 have been reacted with a wide range _ of bifunctional ligands HE E H (E, E =O, S, CO2) giving Os3(m-H) _ (m-EE H)(CO)10 as the major product, the functional groups showing preferential cluster binding as SHWCO2HWOH; increasing the chain length _ increases the chance of forming linked clusters {Os3(m-H)(CO)10}2(m-E E ).41 Organomet Chem., 2010, 36, 182–205 | 193 A series of thianthrene-containing triosmium clusters has been prepared (62–64) The electron deficient complex 63 (L=CO) reversibly adds CO to give 64 and reacts with PPh3 to give 63 (L=PPh3).42 A facile route into Fe, Ru, Os, and Fe2O3 nanoparticles has been reported that involves thermolysis of cluster precursors in ionic liquids; the nanoparticles are in the range 1.5–2.5 nm, and require no extra stabilizers or capping molecules.43 Group Tricobalt carbonyl clusters have been used as end-capping groups for carbon chains containing up to m-C26 units, and including examples linked via a central Hg atom.44 A series of complexes containing Ru(dppe)Cp (Cp =Cp*, Cp) and Co3(m-dppm)(CO)7 linked with C7 chains have been prepared; addition of tcne (tetracyanoethene), tcnq (7,7,8,8-tetracyano-1,4quinodimethane) and Fe2(CO)9 across the central CC bond, and Ni replacement for Co in the Co3 cluster proceed as expected, suggesting the length of the carbon chain prevents any significant interactions between the end groups.45 The octaphosphine polypodal compound 1,2,4,5C6H2{SCH2CH2N(PPh2)2}4 has been used as a central core unit coordinated to four Co3(m3-CCl)(CO)7 or four Co4(m-PPh2XPPh2)(m-CO)3(CO)5 clusters (X=NH, CH2) to form centrosymmetric metal-rich macromolecules.46 Addition of pyridine to Rh4(CO)12 under a CO atmosphere affords the pentanuclear anionic rhodium salt cis-[Rh(CO)2(py)2][Rh5(CO)15] initially; 194 | Organomet Chem., 2010, 36, 182–205 further addition of pyridine results in CO substitution to give cis[Rh(CO)2(py)2][Rh5(CO)15-x(py)x] (x=1, 2) The same reaction with bipyridine gives cis-[Rh(CO)2(bipy)][Rh5(CO)15(bipy)] as the only product In contrast, reaction of Rh4(CO)12 with pyridine under N2 gives Rh6 (CO)16-x(py)x (x=1, 2) NMR spectroscopic studies show that the CO substitution occurs solely on the apical rhodium atom.47 The hexarhodium hydrido cluster [Rh6H12(PPri3)6]2 ỵ reversibly adds water to give the hydroxy hydride derivative [Rh6H11(m-OH)(PPri3)6]2 ỵ 48 The mono- and bis-diphosphine tetrairidium clusters 65 and 66 have been reported; 66 readily loses CO to give the orthometalated 67.49 Group 10 Treatment of trans-PtCl2(PHBut2)2 with NaBH4 affords a mixture of products which slowly convert to the spectroscopically-characterized 68 on standing in ethanol; the complex contains both terminal and bridging hydride ligands.50 A study of the reactivity of [Pt6(m-PBut2)4(CO)6]2 ỵ has shown that the two carbonyls on the edge-bridging Pt atoms are most easily substituted or attacked by nucleophiles A range of derivatives have been reported (69-70), Organomet Chem., 2010, 36, 182–205 | 195 including halo-substituted clusters obtained from treatment with [Bun4N]Cl or with an excess of halide salts.51 10 Group 11 The polymeric 71 (L=Et2O) is formed from reaction of [Au(C6F5)2] À with equimolar AgClO4 in CH2Cl2/Et2O; stirring in thf for 10 mins affords the thf adduct (71, L=thf) which was shown to contain tetranuclear units linked via aurophilic contacts, forming a 1D polymer Both complexes, L=Et2O, thf, together with the previously reported L=NCMe, Me2CO, show characteristic bright colours, ranging from orange through to yellow and green A comparative study of their vapochromic behaviour shows that L=Et2O loses two molecules of coordinated solvent, whereas the other three examples lose less defined volatile organic compounds and fluorinated ligands; in each case, a 1:1 Ag/Au product is obtained Reaction of solid L=Et2O complex with the vapours of the organic solvents used in the preparation of the analogues affords complete substitution in the order NCMeWMe2COWthfWEt2O, and a perceptible change in colour All complexes show luminescence at room temperature and at 77 K in the solid state, assigned to p–p* transitions in the pentafluorophenyl rings.52 11 11.1 Mixed-metal clusters Group The unsaturated methyl complex Mo2(m-Z1:Z2-Me)(m-PCy2)(CO)2 has a weak agostic interaction and undergoes facile dehydrogenation in the presence of metal carbonyl reagents, giving methylidyne-bridged products 196 | Organomet Chem., 2010, 36, 182–205 72 when reacted with Mo(CO)6 under UV-irradiation, or the mixed-metal tetranuclear 73 with Fe2(CO)9 The latter is an unsaturated 60-electron cluster containing a butterfly arrangement of metal atoms.53 Reaction of the dimolybdenum nitrile complex 74 with Ru3(CO)12 in refluxing toluene results in CN bond cleavage to give the m4- and m5nitrido clusters 75 and 76, respectively, in low yield The metal geometry of 76 consists of a distorted bicapped square pyramid with a Ru atom spike, the nitrogen atom lying below the basal Mo2Ru2 plane.54 Heating Cp(CO)(m-CO)2Mo=NiCp* with excess allyldiphenylphosphine affords the trinuclear cluster 77; this 46-electron cluster contains a very short Mo–Mo bond distance, suggesting some multiple-bond character.55 Organomet Chem., 2010, 36, 182–205 | 197 The hexanuclear cluster cation 78 is formed from reaction of 79 (L=Cl) with TlPF6, or directly from a solution of 79 (L=tetrahydrothiophene) at room temperature over 48 h, and consists of an unusual almost planar arrangement of metal atoms and strong p–p-stacking interactions between the cations Interestingly, the structure is maintain in solution.56 11.2 Group Ligand substitution on the 10-vertex metallocarborane [8,10-{Ir(m-PPh2) (Ph)(L)(PPh3)}-8-(m-H)-6,6,6,10,10-(CO)5-closo-6,10,1-Fe2CB7H7]n À (80, L=CO, n=0) with [NEt4]CN affords the anionic complex 80 (L=CN, n=1), which can be treated with cationic metal reagents {CuCl(PPh3)}4 and AuCl(PPh3) to give derivatives with four metal centres (80, L=CN {Cu(PPh3)2}, CN{Au(PPh3)}.57 Reaction of tris(N,N-diethyldithiocarbamato)cobalt with Ru3(CO)12 or Co2(CO)8 affords the thiocarboxamide clusters 81 or 82, containing di- and trimetalated sulfur(diethylamino)carbene ligands, respectively.58 The phosphine thiol cluster RuCo3(m3-H)(CO)11(Ph2PCH2CH2SH) has been anchored to a Au(111) surface, and characterized using scanning tunneling microscopy The cluster was then decarbonylated by controlled thermal annealing to give metallic products containing Ru:Co, in the expected 1:3 ratio, which were characterized by X-ray photoelectron spectroscopy The disulfidelinked octanuclear complex {RuCo3(m3-H)(CO)11(Ph2PCH2CH2S)}2 was also isolated as a by-product during purification.59 Triosmium clusters Os3(m-H)2(CO)10 and Os3(CO)10(NCMe)2 react with {IrCp*Cl2}2 to give a series of mixed-metal Os–Ir clusters 83–90.60,61 198 | Organomet Chem., 2010, 36, 182–205 Reaction of Os3(CO)12 with Pd(PBut3)2 in refluxing octane affords 91, containing Pd(PBut3) groups capping all the triangular faces of a central tetrahedral Os4(CO)12 cluster The complex is electronically unsaturated and reacts readily with H2 to give Os4(m-H)4(CO)12.62 Reaction of Organomet Chem., 2010, 36, 182–205 | 199 Ru3(CO)12 with Pt(PBut3)2 at room temperature affords 92 as the main product, whereas reaction in refluxing hexane affords small amounts of octanuclear cluster 93 and tetranuclear 94 The capped-pentagonal bipyramidal 93 contains 104 cluster electrons, or six fewer than predicted by the Polyhedral Skeletal Electron Pair Theory Solutions of 93 slowly decompose to give a small amount of 93, together with Pt3(CO)3(PBut3)3 No platinum homologue of 91 has yet been isolated.63 The 68 electron unsaturated pentanuclear cluster Os3Pt2(CO)10(PBut3)2 (95) is obtained along with three other products (96–98) from the reaction of Os3(CO)10(NCMe)2 and Pt(PBut3)2 Conversion of 95 to 98 occurs readily at 68 1C with a 50% yield; the transformation involves metallation of one of the methyl groups of the Pt-coordinated But unit Complex 95 adds hydrogen reversibly at 1C, giving the di- and tetra-hydrido clusters 99 and 100 with an Os–Pt bond cleavage on each successive addition of H2 Prolonged exposure of 95 to hydrogen results in degradation of the cluster via loss of one of the Pt(PBut3) units, giving 101–103.64 200 | Organomet Chem., 2010, 36, 182–205 The reactivity of the unsaturated cluster Os3Pt(m4-CHCMeCH) (m-PBut2)(CO)7(PBut3) towards hydrogen, GeHPh3 and PhC2H has been investigated, and three new clusters (104–106) isolated The oxidative addition of H2 occurs at the unsaturated Pt atom and is reversible under mild conditions, whereas the GeHPh3 adds to an osmium atom Addition of phenylacetylene results in loss of the Pt atom to give 106, with the m3-Z5bridging organic ligand acting as a seven-electron donor.65 Organomet Chem., 2010, 36, 182–205 | 201 Reaction of the selenium-capped triiron cluster [Fe3(m3-Se)(CO)9]2 À with 1-3 equivalents of CuX (X=Cl, Br, I) affords clusters incorporating one and two Cu units, 107–108, and the linked clusters [{Fe3(m3-Se)(CO)9}2 (Cu4X2)]2 À (X=Cl, Br) The addition of the CuX to the iron core has been shown to produce a significant anodic shift in the iron oxidation potential The synthesis and electrochemical properties of these clusters have been examined in detail using DFT theory.66 Reaction of [Fe3(m3-Te)(CO)9]2 À with equimolar [Cu(NCMe)4] ỵ at 1C aords the polymeric anionic complex 109, consisting of a zig-zag chain structure, whereas reaction with two equivalents in the presence of 4,4 dipyridine affords 110, containing linked cluster units, and reaction with a 1:3 ratio gives the neutral cluster 111, shown to be the precursor to 109 and 110 The polymeric chains possess significant semiconducting properties.67 Abbreviations bipy Cp Cp* Cy DFT dppe dppm ImAd2 ImDipp 2,2 -bipyridyl Z5-cyclopentadienyl Z5-pentamethylcyclopentadienyl 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Periodical Report a Department of Chemistry, University of York, York YO51 5DD, UK Organomet Chem., 2010, 36, v–v | v ... Cifuentes discuss a selection of highlights on metal cluster chemistry In summary, this volume covers a wide range of organometallic chemistry aligned with important applications in other key areas