Mono- and Bimetallic Ruthenium—Arene Catalysts for Olefin Metathesis: A Survey

[en] In this chapter, we summarize the main achievements of our group toward the development of easily accessible, highly efficient ruthenium—arene catalyst precursors for olefin metathesis. Major advances in this field are presented chronologically, with an emphasis on catalyst design and mechanistic details. The first part of this survey focuses on monometallic complexes with the general formula RuCl2(p-cymene)(L), where L is a phosphine or N-heterocyclic carbene ancillary ligand. In the second part, we disclose recent developments in the synthesis and catalytic applications of homobimetallic ruthenium—arene complexes of generic formula (p-cymene)Ru(μ-Cl)3RuCl(η2-C2H4)(L) and their derivatives resulting from the substitution of the labile ethylene moiety with vinylidene, allenylidene, or indenylidene units

Disciplines :

Chemistry

Author, co-author :

Borguet, Yannick ; Université de Liège - ULiège > Département de chimie (sciences) > Chimie macromoléculaire et catalyse organique

Sauvage, Xavier

Demonceau, Albert ; Université de Liège - ULiège > Département de chimie (sciences) > Chimie macromoléculaire et catalyse organique

Delaude, Lionel ; Université de Liège - ULiège > Département de chimie (sciences) > Chimie macromoléculaire et catalyse organique

Language :

English

Title :

Mono- and Bimetallic Ruthenium—Arene Catalysts for Olefin Metathesis: A Survey

Publication date :

2010

Main work title :

Green Metathesis Chemistry

Editor :

Dragutan, Valerian

Demonceau, Albert ; Université de Liège - ULiège > Département de chimie (sciences)

Dragutan, Ileana

Finkelshtein, Eugene Sh.

Publisher :

Springer, Dordrecht, Netherlands

ISBN/EAN :

978-90-481-3431-1

Collection name :

NATO Science for Peace and Security Series A: Chemistry and Biology

Pages :

89-100

Available on ORBi :

since 27 April 2010

Statistics

Number of views

77 (3 by ULiège)

Number of downloads

0 (0 by ULiège)

More statistics

Scopus citations^®

Scopus citations^®
without self-citations

OpenCitations

Bibliography

Ivin KJ, Mol JC (1997) Olefin metathesis and metathesis polymerization. Academic Press, San Diego CA
Grubbs RH (ed.) (2003) Handbook of metathesis. Wiley-VCH, Weinheim
Nguyen ST, Grubbs RH (1993) Syntheses and activities of new single-component, ruthenium-based olefin metathesis catalysts. J Am Chem Soc 115: 9858-9859
Schwab P, France MB, Ziller JW, Grubbs RH (1995) A series of well-defined metathesis catalysts - synthesis of [RuCl2(=CHR′)(PR 3)2] and its reaction. Angew Chem Int Ed 34: 2039-2041
Weskamp T, Schattenmann WC, Spiegler M, Herrmann WA (1998) A novel class of ruthenium catalysts for olefin metathesis. Angew Chem Int Ed 37: 2490-2493
Huang J, Stevens ED, Nolan SP, Petersen JL (1999) Olefin metathesis-active ruthenium complexes bearing a nucleophilic carbene ligand. J Am Chem Soc 121: 2674-2678
Scholl M, Ding S, Lee CW, Grubbs RH (1999) Synthesis and activity of a new generation of ruthenium-based olefin metathesis catalysts coordinated with 1,3-dimesityl-4,5-dihydroimidazol-2-ylidene ligands. Org Lett 1: 953-956
Trnka TM, Morgan JP, Sanford MS, Wihelm TE, Scholl M, Choi T-L, Ding S, Day MW, Grubbs RH (2003) Synthesis and activity of ruthenium alkylidene complexes coordinated with phosphine and N-heterocyclic carbene ligands. J Am Chem Soc 125: 2546-2558
Love JA, Sanford MS, Day MW, Grubbs RH (2003) Synthesis, structure, and activity of enhanced initiators for olefin metathesis. J Am Chem Soc 125: 10103-10109
Kingsbury JS, Harrity JPA, Bonitatebus PJ, Jr., Hoveyda AH (1999) A recyclable Ru-based metathesis catalyst. J Am Chem Soc 121: 791-799
Garber SB, Kingsbury JS, Gray BL, Hoveyda AH (2000) Efficient and recyclable monomeric and dendritic Ru-based metathesis catalysts. J Am Chem Soc 122: 8168-8179
Wakamatsu H, Blechert S (2002) A highly active and air-stable ruthenium complex for olefin metathesis. Angew Chem Int Ed 41: 794-796
Lynn DM, Mohr B, Grubbs RH, Henling LM, Day MW (2000) Water-soluble ruthenium alkylidenes: synthesis, characterization, and application to olefin metathesis in protic solvents. J Am Chem Soc 122: 6601-6609
Hong SH, Grubbs RH (2006) Highly active water-soluble olefin metathesis catalyst. J Am Chem Soc 128: 3508-3509
Michrowska A, Gułajski Ł, Kaczmarska Z, Mennecke K, Kirschning A, Grela K (2006) A green catalyst for green chemistry: synthesis and application of an olefin metathesis catalyst bearing a quaternary ammonium salt. Green Chem 8: 685-688
Jafarpour L, Heck M-P, Baylon C, Lee HM, Mioskowski C, Nolan SP (2002) Preparation and activity of recyclable polymer-supported ruthenium olefin metathesis catalysts. Organometallics 21: 671-679
Yang L, Mayr M, Wurst K, Buchmeiser MR (2004) Novel metathesis catalysts based on ruthenium 1,3-dimesityl-3,4,5,6-tetrahydropyrimidin-2-ylidenes: synthesis, structure, immobilization, and catalytic activity. Chem Eur J 10: 5761-5770
Michrowska A, Mennecke K, Kunz U, Kirschning A, Grela K (2006) A new concept for the noncovalent binding of a ruthenium-based olefin metathesis catalyst to polymeric phases: preparation of a catalyst on Raschig rings. J Am Chem Soc 128: 13261-13267
Ung T, Hejl A, Grubbs RH, Schrodi Y (2004) Latent ruthenium olefin metathesis catalysts that contain an N-heterocyclic carbene ligand. Organometallics 23: 5399-5401
Hejl A, Day MW, Grubbs RH (2006) Latent olefin metathesis catalysts featuring chelating alkylidenes. Organometallics 25: 6149-6154
Ledoux N, Drozdzak R, Allaert B, Linden A, Van der Voort P, Verpoort F (2007) Exploring new synthetic strategies in the development of a chemically activated Ru-based olefin metathesis catalyst. Dalton Trans: 5201-5210
Trnka TM, Grubbs RH (2001) The development of L2X 2Ru=CHR olefin metathesis catalysts: an organometallic success story. Acc Chem Res 34: 18-29
Hoveyda AH, Gillingham DG, Van Veldhuizen JJ, Kataoka O, Garber SB, Kingsbury JS, Harrity JPA (2004) Ru complexes bearing bidentate carbenes: from innocent curiosity to uniquely effective catalysts for olefin metathesis. Org Biomol Chem 2: 8-23
Deshmukh PH, Blechert S (2007) Alkene metathesis: the search for better catalysts. Dalton Trans 24: 2479-2491
Bieniek M, Michrowska A, Usanov DL, Grela K (2008) In an attempt to provide a user's guide to the galaxy of benzylidene, alkoxybenzylidene, and indenylidene ruthenium olefin metathesis catalysts. Chem Eur J 14: 806-818
Boeda F, Clavier H, Nolan SP (2008) Ruthenium-indenylidene complexes: powerful tools for metathesis transformations. Chem Commun: 2726-2740
Seiders TJ, Ward DW, Grubbs RH (2001) Enantioselective ruthenium-catalyzed ring-closing metathesis. Org Lett 3: 3225-3228
Van Veldhuizen JJ, Gillingham DG, Garber SB, Kataoka O, Hoveyda AH (2003) Chiral Ru-based complexes for asymmetric olefin metathesis: enhancement of catalyst activity through steric and electronic modifications. J Am Chem Soc 125: 12502-12508
Funk TW, Berlin JM, Grubbs RH (2006) Highly active chiral ruthenium catalysts for asymmetric ring-closing olefin metathesis. J Am Chem Soc 128: 1840-1846
Love JA, Morgan JP, Trnka TM, Grubbs RH (2002) A practical and highly active ruthenium-based catalyst that effects the cross metathesis of acrylonitrile. Angew Chem Int Ed 41: 4035-4037
Hérisson J-L, Chauvin Y (1971) Catalysis of olefin transformation by tungsten complexes. II telomerization of cyclic olefins in the presence of acyclic olefins. Makromol Chem 141: 161-176
Katayama H, Ozawa F (2004) Vinylideneruthenium complexes in catalysis. Coord Chem Rev 248: 1703-1715
Dragutan V, Dragutan I (2004) Ruthenium vinylidene complexes. Synthesis and applications in metathesis catalysis. Platinum Met Rev 48: 148-153
Bruneau C, Dixneuf PH (2006) Metal vinylidenes and allenylidenes in catalysis: applications in anti-Markovnikov additions to terminal alkynes and alkene metathesis. Angew Chem Int Ed 45: 2176-2203
Dragutan V, Dragutan I, Verpoort F (2005) Ruthenium indenylidene complexes. Metathesis catalysts with enhanced activity. Platinum Met Rev 49: 33-40
Clavier H, Nolan SP (2007) N-heterocyclic carbene and phosphine ruthenium indenylidene precatalysts: a comparative study in olefin metathesis. Chem Eur J 13: 8029-8036
Jones D, Pratt L, Wilkinson G (1962) π-Cyclohexadienyl compounds of manganese, rhenium, iron, and ruthenium. J Chem Soc: 4458-4463
Winkhaus G, Singer H (1967) Ruthenium(II) complexes with bidentate cycloheptatriene and benzene. J Organomet Chem 7: 487-491
Zelonka RA, Baird MC (1972) Benzene complexes of ruthenium(II). Can J Chem 50: 3063-3072
Bennett MA, Smith AK (1974) Arene ruthenium(II) complexes formed by dehydrogenation of cyclohexadienes with ruthenium(III) trichloride. J Chem Soc, Dalton Trans: 233-241
Le Bozec H, Touchard D, Dixneuf PH (1989) Organometallic chemistry of arene ruthenium and osmium complexes. Adv Organomet Chem 29: 163-247
Bennett MA (1997) Recent advances in the chemistry of arene complexes of ruthenium(0) and ruthenium(II). Coord Chem Rev 166: 225-254
Pigge FC, Coniglio JJ (2001) Stoichiometric applications of η6-arene ruthenium(II) complexes in organic chemistry. Curr Org Chem 5: 757-784
Rigby JH, Kondratenko MA (2004) Arene complexes as catalysts. Top Organonomet Chem 7: 181-204
Therrien B (2009) Functionalised η6-arene ruthenium complexes. Coord Chem Rev 253: 493-519
Küçükbay H, Çetinkaya B, Guesmi S, Dixneuf PH (1996) New (carbene)ruthenium-arene complexes: preparation and uses in catalytic synthesis of furans. Organometallics 15: 2434-2439
Çetinkaya B, Özdemir I, Dixneuf PH (1997) Synthesis and catalytic properties of Nfunctionalized carbene complexes of rhodium(I) and ruthenium(II). J Organomet Chem 534: 153-158
Fürstner A, Müller T (1999) Efficient total synthesis of resin glycosides and analogues by ring-closing olefin metathesis. J Am Chem Soc 121: 7814-7821
Castarlenas R, Dixneuf PH (2003) Highly active catalysts in alkene metathesis: first observed transformation of allenylidene into indenylidene via alkenylcarbyne-ruthenium species. Angew Chem Int Ed 42: 4524-4527
Castarlenas R, Eckert M, Dixneuf PH (2005) Alkenylcarbene ruthenium arene complexes as initiators of alkene metathesis: an enyne creates a catalyst that promotes its selective transformation. Angew Chem Int Ed 44: 2576-2579
Yiǧit M, Yiǧit B, Özdemir I, Çetinkaya E, Çetinkaya B (2006) Active ruthenium-(N-heterocyclic carbene) complexes for hydrogenation of ketones. Appl Organomet Chem 20: 322-327
Quebatte L, Haas M, Solari E, Scopelliti R, Nguyen QT, Severin K (2005) Atom-transfer radical reactions under mild conditions with [{RuCl 2(1,3,5-C6H3iPr3)}2] and PCy3 as the catalyst precursors. Angew Chem Int Ed 44: 1084-1088
Hafner A, Mühlebach A, van der Schaaf PA (1997) One-component catalysts for thermal and photoinduced ring opening metathesis polymerization. Angew Chem Int Ed 36: 2121-2124
Fürstner A, Ackermann L (1999) A most user-friendly protocol for ring closing metathesis reactions. Chem Commun: 95-96
Fürstner A, Liebl M, Lehmann CW, Picquet M, Kunz R, Bruneau C, Touchard D, Dixneuf PH (2000) Cationic ruthenium allenylidene complexes as catalysts for ring closing olefin metathesis. Chem Eur J 6: 1847-1857
Simal F, Demonceau A, Noels AF (1999) Highly efficient ruthenium-based catalytic systems for the controlled free-radical polymerization of vinyl monomers. Angew Chem Int Ed 38: 538-540
Simal F, Jan D, Delaude L, Demonceau A, Spirlet M-R, Noels AF (2001) Evaluation of ruthenium-based complexes for the controlled radical polymerization of vinyl monomers. Can J Chem 79: 529-535
Delaude L, Delfosse S, Richel A, Demonceau A, Noels AF (2003) Tuning of ruthenium N-heterocyclic catalysts for ATRP. Chem Commun: 1526-1527
Richel A, Delfosse S, Cremasco C, Delaude L, Demonceau A, Noels AF (2003) Ruthenium catalysts bearing N-heterocyclic carbene ligands in atom transfer radical reactions. Tetrahedron Lett 44: 6011-6015
Borguet Y, Richel A, Delfosse S, Leclerc A, Delaude L, Demonceau A (2007) Microwave-enhanced ruthenium-catalysed atom transfer radical additions. Tetrahedron Lett 48: 6334-6338
Simal F, Demonceau A, Noels AF (1999) Kharasch addition and controlled atom transfer radical polymerisation (ATRP) of vinyl monomers catalysed by Grubbs' ruthenium-carbene complexes. Tetrahedron Lett 40: 5689-5693
Simal F, Delfosse S, Demonceau A, Noels AF, Denk K, Kohl FJ, Weskamp T, Herrmann WA (2002) Ruthenium alkylidenes: modulation of a new clas of catalysts for controlled radical polymerization of vinyl monomers. Chem Eur J 8: 3047-3052
Demonceau A, Noels AF, Saive E, Hubert AJ (1992) Ruthenium-catalysed ring-opening metathesis polymerization of cycloolefins initiated by diazoesters. J Mol Catal 76: 123-132
Stumpf AW, Saive E, Demonceau A, Noels AF (1995) Ruthenium-based catalysts for the ring-opening metathesis polymerization of low-strain cyclic olefins and of functionalised derivatives of norbornene and cyclooctene. Chem Commun: 1127-1128
Demonceau A, Stumpf AW, Saive E, Noels AF (1997) Novel ruthenium-based catalyst systems for the ring-opening metathesis polymerization of low-strain cyclic olefins. Macromolecules 30: 3127-3136
Ahr M, Thieuleux C, Copéret C, Fenet B, Basset J-M (2007) Noels' vs. Grubbs' catalysts: evidence for one unique active species from two different systems! Adv Synth Catal 349: 1587-1591
Delaude L, Demonceau A, Noels AF (2001) Visible light induced ring-opening metathesis polymerisation of cyclooctene. Chem Commun: 986-987
Jan D, Delaude L, Simal F, Demonceau A, Noels AF (2000) Synthesis and evaluation of new RuCl2(p-cymene)(ER2R′) and (η1:η6-phosphinoarene)RuCl2 complexes as ring-opening metathesis polymerization catalysts. J Organomet Chem 606: 55-64
Tudose A, Demonceau A, Delaude L (2006) Imidazol(in)ium-2-carboxylates as N-heterocyclic carbene precursors in ruthenium-arene catalysts for olefin metathesis and cyclopropanation. J Organomet Chem 691: 5356-5365
Quebatte L, Solari E, Scopelliti R, Severin K (2005) A bimetallic ruthenium ethylene complex as a catalyst precursor for the Kharasch reaction. Organometallics 24: 1404-1406
Sauvage X, Borguet Y, Noels AF, Delaude L, Demonceau A (2007) Homobimetallic ruthenium-N-heterocyclic carbene complexes: synthesis, characterization, and catalytic applications. Adv Synth Catal 349: 255-265
Sauvage X, Borguet Y, Zaragoza G, Demonceau A, Delaude L (2009) Homobimetallic ruthenium vinylidene, allenylidene, and indenylidene complexes: synthesis, characterization, and catalytic studies. Adv Synth Catal 351: 441-455
Harlow KJ, Hill AF, Wilton-Ely JDET (1999) The first co-ordinatively unsaturated Group 8 allenylidene complexes: insights into Grubbs' vs. Dixneuf-Fürstner olefin metathesis catalysts. J Chem Soc, Dalton Trans: 285-291
Fürstner A, Hill AF, Liebl M, Wilton-Ely JDET (1999) Coordinatively unsaturated ruthenium-allenylidene complexes: highly effective, well defined catalysts for the ring-closure metathesis of α,ω-dienes and dienynes. Chem Commun: 601-602
Fürstner A, Guth O, Düffels A, Seidel G, Liebl M, Gabor B, Mynott R (2001) Indenylidene complexes of ruthenium: optimized synthesis, structure elucidation, and performance as catalysts for olefin metathesis - application to the synthesis of the ADE-ring system of Nakadomarin A. Chem Eur J 7: 4811-4820