Ruthenium(II) supported by phosphine-functionalized N-heterocyclic carbene ligands as catalysts for the transfer hydrogenation of ketones

Inorganic Chemistry Communications

Volumn 37, Issue , 2013, Pages 138-143

  Humphries, Matthew E ^a   Pecak, Wiktoria H ^a,c   Hohenboken, Sallie A ^a   Alvarado, Samuel R ^a,d   Swenson, Dale C ^b   Domski, Gregory J ^a  

^a AUGUSTANA COLLEGE   (United States)

^b UNIVERSITY OF IOWA   (United States)

^c UNIVERSITY OF ILLINOIS AT CHICAGO   (United States)

^d IOWA STATE UNIVERSITY   (United States)

Author keywords

N heterocyclic carbene; Ortho metalation; Ruthenium(II) complexes; Transfer hydrogenation

Indexed keywords

EID: 84885556816     PISSN: 13877003     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.inoche.2013.09.046     Document Type: Article

References (40)

1. A.J. Arduengo, R.L. Harlow, and M. Kline A stable crystalline carbene J. Am. Chem. Soc. 113 1991 361 363
2. W.A. Herrmann, M. Elison, J. Fischer, C. Köcher, and G.R.J. Artus Metal complexes of N-heterocyclic carbenes - a new structural principle for catalysts in homogeneous catalysis Angew. Chem. Int. Ed. Engl. 34 1995 2371 2374
3. T. Weskamp, F.J. Kohl, W. Hieringer, D. Gleich, and W.A. Herrmann Highly active ruthenium catalysts for olefin metathesis: the synergy of N-heterocyclic carbenes and coordinatively labile ligands Angew. Chem. Int. Ed. 38 1999 2416 2419 (Pubitemid 29399580)
4. T. Weskamp, W.C. Schattenmann, M. Spiegler, and W.A. Herrmann A novel class of ruthenium catalysts for olefin metathesis Angew. Chem. Int. Ed. 37 1998 2490 2493 (Pubitemid 28485877)
5. L. Ackermann, A. Fürstner, T. Weskamp, F.J. Kohl, and W.A. Herrmann Ruthenium carbene complexes with imidazolin-2-ylidene ligands allow the formation of tetrasubstituted cycloalkenes by RCM Tetrahedron Lett. 40 1999 4787 4790 (Pubitemid 29281783)
6. D. Enders, H. Gielen, G. Raabe, J. Runsink, and J.H. Teles Synthesis and stereochemistry of the first chiral (imidazolinylidene)- and (triazolinylidene)palladium(II) complexes Chem. Ber. 129 1996 1483 1488 (Pubitemid 126755767)
7. J. Henrique Teles, J.-P. Melder, K. Ebel, R. Schneider, E. Gehrer, W. Harder, S. Brode, D. Enders, K. Breuer, and G. Raabe The chemistry of stable carbenes. Part 2. Benzoin-type condensations of formaldehyde catalyzed by stable carbenes Helv. Chim. Acta 79 1996 61 83 (Pubitemid 126500194)
8. H. Kücükbay, B. Çetinkaya, S. Guesmi, and P.H. Dixneuf New (carbene) ruthenium‚ arene complexes: preparation and uses in catalytic synthesis of furans Organometallics 15 1996 2434 2439 (Pubitemid 126540198)
9. J. Huang, E.D. Stevens, S.P. Nolan, and J.L. Petersen Olefin metathesis-active ruthenium complexes bearing a nucleophilic carbene ligand J. Am. Chem. Soc. 121 1999 2674 2678 (Pubitemid 29165503)
10. M. Scholl, S. Ding, C.W. Lee, and R.H. Grubbs 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 1999 953 956
11. M. Scholl, T.M. Trnka, J.P. Morgan, and R.H. Grubbs Increased ring closing metathesis activity of ruthenium-based olefin metathesis catalysts coordinated with imidazolin-2-ylidene ligands Tetrahedron Lett. 40 1999 2247 2250 (Pubitemid 29113121)
12. W.A. Herrmann N-heterocyclic carbenes: a new concept in organometallic catalysis Angew. Chem. Int. Ed. 41 2002 1290 1309 (Pubitemid 34437411)
13. A.T. Normand, and K.J. Cavell Donor-functionalised N-heterocyclic carbene complexes of group 9 and 10 metals in catalysis: trends and directions Eur. J. Inorg. Chem. 2008 2008 2781 2800
14. A.J. Blacker Enantioselective transfer hydrogenation C.J.E. Johannes, G. De Vries, The handbook of homegenous hydrogenation 2007 Wiley-VCH Weinheim
15. T. Ikariya, and A.J. Blacker Asymmetric transfer hydrogenation of ketones with bifunctional transition metal-based molecular catalysts Acc. Chem. Res. 40 2007 1300 1308
16. Y. Cheng, J.-F. Sun, H.-L. Yang, H.-J. Xu, Y.-Z. Li, X.-T. Chen, and Z.-L. Xue Syntheses, structures, and catalytic properties of ruthenium(II) nitrosyl complexes with pyridine-functionalized N-heterocyclic carbenes Organometallics 28 2009 819 823
17. W.B. Cross, C.G. Daly, Y. Boutadla, and K. Singh Variable coordination of amine functionalised N-heterocyclic carbene ligands to Ru, Rh and Ir: C-H and N-H activation and catalytic transfer hydrogenation Dalton Trans. 40 2011 9722 9730
18. W.W.N. Ou, A.J. Lough, and R.H. Morris The hydrogenation of molecules with polar bonds catalyzed by a ruthenium(II) complex bearing a chelating N-heterocyclic carbene with a primary amine donor Chem. Commun. 46 2010 8240 8242
19. F. Zeng, and Z. Yu Ruthenium(II) complexes bearing a pyridyl-supported pyrazolyl,N-heterocyclic carbene (NNC) ligand and their catalytic activity in the transfer hydrogenation of ketones Organometallics 27 2008 6025 6028
20. A. Sinha, P. Daw, S.M.W. Rahaman, B. Saha, and J.K. Bera A Ru(II)-N-heterocyclic carbene (NHC) complex from metal-metal singly bonded diruthenium(I) precursor: synthesis, structure and catalytic evaluation J. Organomet. Chem. 696 2011 1248 1257
21. W.W.N. Ou, A.J. Lough, and R.H. Morris Transmetalation of a primary amino-functionalized N-heterocyclic carbene ligand from an axially chiral square-planar nickel(II) complex to a ruthenium(II) precatalyst for the transfer hydrogenation of ketones Organometallics 28 2009 6755 6761
22. M. Poyatos, J.A. Mata, E. Falomir, R.H. Crabtree, and E. Peris New ruthenium(II) CNC-pincer bis(carbene) complexes: synthesis and catalytic activity Organometallics 22 2003 1110 1114
23. M. Poyatos, A. Maisse-François, S. Bellemin-Laponnaz, E. Peris, and L.H. Gade Synthesis and structural chemistry of arene-ruthenium half-sandwich complexes bearing an oxazolinyl-carbene ligand J. Organomet. Chem. 691 2006 2713 2720 (Pubitemid 43669020)
24. F.E. Fernández, M.C. Puerta, and P. Valerga Half-sandwich ruthenium(II) picolyl-NHC complexes: synthesis, characterization, and catalytic activity in transfer hydrogenation reactions Organometallics 30 2011 5793 5802
25. F.E. Fernández, M.C. Puerta, and P. Valerga Ruthenium(II) picolyl-NHC complexes: synthesis, characterization, and catalytic activity in amine N-alkylation and transfer hydrogenation reactions Organometallics 31 2012 6868 6879
26. X.-W. Li, F. Chen, W.-F. Xu, Y.-Z. Li, X.-T. Chen, and Z.-L. Xue Syntheses, structures and catalytic activities of ruthenium (II) carbonyl iodide complexes with CNC-pincer bis (carbene) ligand Inorg. Chem. Commun. 14 2011 1673 1676
27. Y. Cheng, H.-J. Xu, J.-F. Sun, Y.-Z. Li, X.-T. Chen, and Z.-L. Xue Synthesis, structures and catalytic activities of ruthenium(II) carbonyl chloride complexes containing pyridine-functionalised N-heterocyclic carbenes Dalton Trans. 2009 7132 7140
28. W. Baratta, J. Schütz, E. Herdtweck, W.A. Herrmann, and P. Rigo Fast transfer hydrogenation using a highly active orthometalated heterocyclic carbene ruthenium catalyst J. Organomet. Chem. 690 2005 5570 5575 (Pubitemid 41635906)
29. S. Burling, B.M. Paine, D. Nama, V.S. Brown, M.F. Mahon, T.J. Prior, P.S. Pregosin, M.K. Whittlesey, and J.M.J. Williams CH activation reactions of ruthenium N-heterocyclic carbene complexes: application in a catalytic tandem reaction involving CC bond formation from alcohols J. Am. Chem. Soc. 129 2007 1987 1995
30. S. Horn, C. Gandolfi, and M. Albrecht Transfer hydrogenation of ketones and activated olefins using chelating NHC ruthenium complexes Eur. J. Inorg. Chem. 2011 2011 2863 2868
31. J. DePasquale, N.J. White, E.J. Ennis, M. Zeller, J.P. Foley, and E.T. Papish Synthesis of chiral N-heterocyclic carbene (NHC) ligand precursors and formation of ruthenium(II) complexes for transfer hydrogenation catalysts Polyhedron 58 2013 162 170
32. NHCP ligand: silver and ruthenium complexes, facial/meridional coordination, and catalytic transfer hydrogenation Organometallics 24 2005 1692 1702 (Pubitemid 40448888)
33. V. Miranda-Soto, D.B. Grotjahn, A.L. Cooksy, J.A. Golen, C.E. Moore, and A.L. Rheingold A labile and catalytically active imidazol-2-yl fragment system Angew. Chem. Int. Ed. 50 2011 631 635
34. N. Gürbüz, S. Yaşar, E.Ö. Özcan, İ. Özdemir, and B. Çetinkaya Transfer hydrogenation of ketones by ruthenium complexes bearing benzimidazol-2-ylidene ligands Eur. J. Inorg. Chem. 2010 2010 3051 3056
35. S. Demir, I. Özdemir, B. Çetinkaya, E. Sahin, and C. Arici Synthesis, characterization, and application to transfer hydrogenation of η6-(3,4,5-trimethoxybenzyl)- η1-N -heterocyclic carbene†š ruthenium complex J. Coord. Chem. 64 2011 2565 2572
36. B. Yigit, M. Yigit, I. Özdemir, and E. Çetinkaya Synthesis of ruthenium(II) N-heterocyclic carbene complexes and their catalytic activities in transfer hydrogenation of ketones Transit. Met. Chem. 37 2012 297 302
37. A.-E. Wang, J.-H. Xie, L.-X. Wang, and Q.-L. Zhou Triaryl phosphine-functionalized N-heterocyclic carbene ligands for Heck reaction Tetrahedron 61 2005 259 266 (Pubitemid 39573424)
38. F. Stiemke, M. Gjikaj, and D.E. Kaufmann Novel triphenylarsinyl- functionalized N-heterocyclic carbene ligands in palladium-catalyzed C-C coupling reactions J. Organomet. Chem. 694 2009 5 13
39. G.J. Domski, S.A. Hohenboken, and D.C. Swenson Rac-cis, cis-dicarbonyldichlorido{1-[2-(diphenylphosphanyl)benzyl]-3-mesityl-imidazol-2- yl-idene}ruthenium(II) dichloromethane monosolvate Acta Crystallogr. E Struct. Rep. Online 68 2012 m1121
40. 2}ruthenium(II) dichloromethane monosolvate Acta Crystallogr. E Struct. Rep. Online 68 2012 m1224 m1225