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Kinetic and structural studies on 'tethered' Ru(II) arene ketone reduction catalysts

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Cheung, Fung Kei, Clarke, Adam J., Clarkson, Guy J., Fox, David J., Graham, Mark A., Lin, Changxue, Crivillé, Adriana Lorente and Wills, Martin. (2010) Kinetic and structural studies on 'tethered' Ru(II) arene ketone reduction catalysts. Dalton Transactions, Vol.39 (No.5). pp. 1395-1402. ISSN 1477-9226

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Official URL: http://dx.doi.org/10.1039/b915932k

Abstract

A series of kinetic and structural investigations on ruthenium-based catalysts for asymmetric transfer hydrogenation (ATH) of ketones are reported. A method is reported for monitoring the formation of ruthenium hydride species in real time using H-1 NMR spectroscopy.

Item Type:	Journal Article
Subjects:	Q Science > QD Chemistry
Divisions:	Faculty of Science > Chemistry
Library of Congress Subject Headings (LCSH):	Catalysts -- Analysis, Ruthenium, Ketones
Journal or Publication Title:	Dalton Transactions
Publisher:	Royal Society of Chemistry
ISSN:	1477-9226
Date:	2010
Volume:	Vol.39
Number:	No.5
Number of Pages:	8
Page Range:	pp. 1395-1402
Identification Number:	10.1039/b915932k
Status:	Peer Reviewed
Publication Status:	Published
Access rights to Published version:	Restricted or Subscription Access
Funder:	Engineering and Physical Sciences Research Council (EPSRC), AstraZeneca (Firm), British Council
Grant number:	GR/S72214/1 (EPSRC), EP/D072182/1 (EPSRC)
References:	1. (a) M. J. Palmer and M. Wills, Tetrahedron: Asymmetry 1999, 10, 2045. (b) R. Noyori and S. Hashiguchi, Acc. Chem. Res. 1997, 30, 97. (c) S. E. Clapham, A. Hadzovic and R. H. Morris, Coord. Chem. Rev. 2004, 248, 2201. (d) G. Zassinovich, G. Mestroni and S. 40 Gladiali, Chem. Rev. 1992, 92, 1051. (e) S. Gladiali and E. Alberico, Chem. Soc. Rev. 2006, 35, 226. (f) T. Ikariya, K. Murata and R. Noyori, Org. Biomol. Chem. 2006, 4, 393. (g) T. Ikariya and A. J. Blacker, Acc. Chem. Res. 2007, 40, 1300 2. (a) S. Hashiguchi, A. Fujii, J. Takehara, T. Ikariya and R. Noyori, J. Am. Chem. Soc. 1995, 117, 7562. (b) A. Fujii, S. Hashiguchi, N. Uematsu, T. Ikariya and R. Noyori, J. Am. Chem. Soc. 1996, 118, 2521. (c) K. Matsumura, S. Hashiguchi, T. Ikariya and R. Noyori, R. J. Am. Chem. Soc. 1997, 119, 8738. (d) K. Murata, K. Okano, M. Miyagi, H. Iwane, R. Noyori and T. Ikariya, Org. Lett. 1999, 1, 1119. (e) K. J. Haack, S. Hashiguchi, A. Fujii, T. Ikariya and Noyori, Angew. Chem. Int. Ed. 1997, 36, 285. 3. (a) M. Yamakawa, I. Yamada and R. Noyori, Angew. Chem. Int. Ed. 2001, 40, 2818. (b) R. Noyori, M. Yamakawa and S. Hashiguchi, J. Org. Chem. 2001, 66, 7931. (c) M. Yamakawa, H. Ito and R. Noyori, J. Am. Chem. Soc. 2000, 122, 1466. (d) D. A. Alonso, P. Brandt, S. J. M. Nordin and P. G. Andersson, J. Am. Chem. Soc. 1999, 121, 9580 (graph of rate vs dihedral angle). (e) P. Brandt, P. Roth and P. G. Andersson, J. Org. Chem. 2004, 69, 4885. (f) J.-W. Handgraaf and E. J. Meijer, J. Am. Chem. Soc. 2007, 129, 3099-3103. 4. (a) M. Wills, in „Modern Reduction methods‟, ed. P. G. Andersson and I. J. Munslow, pp271, Wiley-VCH, Weinheim, 2008. (b) D. G. Blackmond, M. Ropic and M. Stefinvic, M. Org. Proc. Res. Dev. 2006, 10, 457. (c) N. Uematsu, A. Fujii, S. Hashiguchi, T. Ikariya and R. Noyori, J. Am. Chem. Soc. 1996, 118, 4916. (d) G. D. Williams, C. E. Wade and M. Wills, Chem. Commun. 2005, 4735. (a) J. B. Åberg, J. S. M. Samec and J.-E. Bäckvall, Chem. Commun. 2006, 2771. 5. (a) F. K. Cheung, C. Lin, F. Minissi, A. L. Criville, M. A. Graham, D. J. Fox and Wills, M. Org. Lett. 2007, 9, 4659. (b) A. M. Hayes, D. J. Morris, G. J. Clarkson and M. Wills, J. Am. Chem. Soc. 2005, 127, 7318. (c) J. Hannedouche, G. J. Clarkson and M. Wills, J. Am. Chem. Soc., 2004, 126, 986. (d) J. E. D. Martins, G. J. Clarkson and M. Wills, Org. Lett. 2009, 11, 847. (e) F. K. Cheung, A. M. Hayes, D. J. Morris and M. Wills, Org. Biomol. Chem. 2007, 5, 1093. (f) D. J. Morris, A. M. Hayes and M. Wills, J. Org. Chem., 2006, 71, 7035. 6. (a) J. Wettergren, E. Buitrago, P. Ryberg and H. Adolfsson, Chem. Eur. J. 2009, 15, 5709. (b) I. Plantan, M. Stephan, U. Urleb and B. Mohar, Tetrahedron Lett. 2009, 50, 2676. (c) W. Baratta, G. Chelucci, S. Magnolia, K. Siega and P. Riga, Chem. Eur. J. 2009, 15, 726. (d) J. Zhang, P. G. Biazecka, M. M. Bruendl and Y. Huang, J. Org. Chem. 2009, 74, 1411. (e) Z. Ding, J. Yang, T. Wang, Z. Shen and Y. Zhang, Chem. Commun. 2009, 571. (f) M. B. Díaz-Valenzuela, S. D. Phillips, M. B. France, M. E. Gunn and M. L. Clarke, Chem. Eur. J. 2009, 15, 1227. (g) X. Wu, J. Liu, D. D. Tommaso, J. A. Iggo, C. R. A. Catlow, J. Basca and J. Xiao, Chem. Eur. J. 2008, 15, 7699. (h) A. Cortez, C. Z. Flores-López, R. Rodríquez-Apodaca, L. Z. Flores-López, M. Parra-Hake and R. Somananthan, ARKIVOC, 2005, 162. (i) A. V. Gaikwad, V. boffa, J. E. ten Elshof and G. Rothenberg, Angew. Chem. Int. Ed. 2008, 47, 5407. (j) H. Takamura, J. Ando, T. Abe, T. Murata. I. Kadota and D. Uemura, Tetrahedron Lett. 2008, 49, 4626. (k) C. Wang, X. Wu and J. Xiao, Chem. Asian J. 2008, 3, 1750. (l) A. Pordea and T. R. Ward, Chem. Commun. 2008, 4239. (m) J. Wettergren, A. B. Zaitsev and H. Adolfsson, Adv. Synth. Catal. 2007, 349, 2556. 7. (a) Koike, T.; Ikariya, T. Adv. Synth. Catal. 2004, 346, 37. (b) Koike, T.; Ikariya, T. J. Organomet. Chem. 2007, 692, 408. 8. We thank a referee for making the observation that for the runs at 2M PhCOMe and above, the initial rate (slope) is essentially constant, at ca. 0.05 M min-1. This limiting rate should be equal to k2[9] (assuming rate determining k2) and so k2 can be obtained by simply dividing the rate by catalyst concentration (0.01 M) to give k2 = ca. 5 min-1, which matches the curve-fitting calculation quite closely. 9. (a) C. P. Casey, T. B. Clark and I. A. Guzei, J. Am. Chem. Soc. 2007, 129, 11821. (b) J. S. M. Samec, A. H. Éll, J. B. Åberg, T. Primalov, L. Eriksson and J.-E. Bäckvall, J. Am. Chem. Soc. 2006, 128, 14293. (c) C. P. Casey and J. B. Johnson, J. Am. Chem. Soc. 2005, 127, 1883. (d) C. P. Casey, S. E. Beetner and J. B. Johnson, J. Am. Chem. Soc. 2008, 130, 2285 (e) J. Nyhlén, T. Primalov and J.-E. Bäckvall, Chem. Eur. J. 2009, 15, 5220. (f) D. Mavrynsky, R. Sillanpää and R. Leino, Organometallics, 2009, 28, 598. (g) A. Comas-Vives, G. Ujaque and A. Lledós, Organometallics, 2007, 26, 4135. (h) B. Martín-Matute, J. B. Åberg, M. Edin and J.-E. Backvall, Chem. Eur. J. 2007, 13, 6063. (i) A. Dijksman, J. M. Elzinga, Y.-X. Li, I. W. C. E. Arends and R. A. Sheldon, Tetrahedron: Asymmetry, 2002, 13, 879. 10. (a) Y. Himeda, N. Onozawa-Komatsuzaki, H. Sugihara, H. Arakawa, and K. Kasuga, J. Mol.Catal. A. Chemical 2003, 195, 95. (b) Soleimannejad, J.; Sisson, A.; White, C. Inorg. Chim. Acta. 2003, 121. 11. D. J. Morris and M. Wills, Organometallics, 2009, 28, 4133–4140. 12. D. A. Fletcher, R. F. McMeeking and D. Parkin, J. Chem. Inf. Comput. Sci. 1996, 36, 746.
URI:	http://wrap.warwick.ac.uk/id/eprint/6528