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Ether-tethered Ru(ii)/TsDPEN complexes : synthesis and applications to asymmetric transfer hydrogenation

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Parekh, Vimal, Ramsden, James A. and Wills, Martin. (2012) Ether-tethered Ru(ii)/TsDPEN complexes : synthesis and applications to asymmetric transfer hydrogenation. Catalysis Science & Technology, Vol.2 (No.2). pp. 406-414. ISSN 2044-4753

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Official URL: http://dx.doi.org/10.1039/C1CY00364J

Abstract

A new type of Ru(II)/TsDPEN catalyst containing an ether-based linking tether has been prepared and shown to exhibit excellent activity in asymmetric transfer hydrogenation reactions of ketones. Related complexes containing a hydroxyl-terminated alkyl chain have also been prepared and tested as asymmetric catalysts. In some cases the activity of the new catalyst type complements that of the closely related alkyl-chain tethered complexes.

Item Type: Journal Article
Subjects: Q Science > QD Chemistry
Divisions: Faculty of Science > Chemistry
Library of Congress Subject Headings (LCSH): Ruthenium compounds, Metal catalysts, Hydrogenation, Ketones
Journal or Publication Title: Catalysis Science & Technology
Publisher: Royal Society of Chemistry
ISSN: 2044-4753
Date: 2012
Volume: Vol.2
Number: No.2
Page Range: pp. 406-414
Identification Number: 10.1039/c1cy00364j
Status: Peer Reviewed
Publication Status: Published
Access rights to Published version: Restricted or Subscription Access
Funder: Engineering and Physical Sciences Research Council (EPSRC), Dr. Reddy's Laboratories
References: 1. (a) V. Caprio and J. M. J. Williams, Catalysis in Asymmetric Synthesis, 2nd Edition, Wiley, Chichester UK, 2009. (b) R. Noyori, Asymmetric Catalysis in Organic Synthesis, Wiley, New York, 1994. (c) I. Ojima, Catalytic Asymmetric Synthesis, 2nd Edition, Wiley, New York, 2000. (d) J. F. Hartwig, Organotransition Metal Chemistry: From Bonding to Catalysis, University Science Books, Sausalito, 2009. (e) E. Jacobsen, A. Pfaltz, and H. Yamamoto, Comprehensive Asymmetric Catalysis, Springer Press, Heidelberg, 1999. 2 (a) T. Ikariya, K. Murata and R. Noyori, Org. Biomol. Chem. 2006, 4, 393-406. (b) S. Gladiali and E. Alberico, Chem. Soc. Rev. 2006, 36, 226-236. (c) T. Ikariya and A. J. Blacker, Acc. Chem. Res. 2007, 40, 1300-1308. (d) S. E. Clapham, A. Hadzovic and R. H. Morris, Coord. Chem. Rev. 2004, 248, 2201-2237. (e) S. Hashiguchi and R. Noyori, Acc. Chem. Res. 1997, 30, 97-102. (f) C. Wang, X. F. Wu and J. L. Xiao, Chem. Asian J. 2008, 3, 1750-1770. (g) M. J. Palmer and M. Wills, Tetrahedron: Asymmetry 1999, 10, 2045-2061. (h) R. Noyori and S. Hashiguchi, Acc. Chem. Res. 1997, 30, 97-102. (i) R. Noyori, Angew. Chem. Int. Ed. 2002, 41, 2008-2022. 3. (a) S. Hashiguchi, A. Fujii, J. Takehara, T. Ikariya, R. Noyori, J. Am. Chem. Soc. 1995, 117, 7562-7563. (b) A. Fujii, S. Hashiguchi, N. Uematsu, T. Ikariya, R. Noyori, J. Am. Chem. Soc. 1996, 118, 2521-2522. (c) K. Matsumura, S. Hashiguchi, T. Ikariya, R. Noyori, J. Am. Chem. Soc. 1997, 119, 8738-8739. (d) K. Murata, K. Okano, M. Miyagi, H. Iwane, R. Noyori, T. Ikariya, Org. Lett. 1999, 1, 1119-1121. (e) K. J. Haack, S. Hashiguchi, A. Fujii, T. Ikariya, R. Noyori, Angew. Chem. Int. Ed. 1997, 36, 285-288. 4. (a) Y.-M. He and Q.-H. Fan, Org. Biomol. Chem. 2010, 8, 2497-2504. (b) M. Ito and T. Ikariya, Chem. Commun. 2007, 5134-5142. (c) T. Ohkuma, N. Utsumi, K. Tsutsumi, K. Murata, C. Sandoval and R. Noyori, J. Am. Chem. Soc. 2006, 128, 8724-8725. (d) C. A. Sandoval, T. Ohkuma, N. Utsumi, K. Tsutsumi, K. Murara and R. Noyori, Chem. Asian. J. 2006, 1-2, 102-110. (e) T. Ohkuma, K. Tsutsumi, N. Utsumi, N. Arai, R. Noyori and K. Murata, Org. Lett. 2007, 9, 255-257. (f) T. Ohkuma, N. Utsumi, M. Watanabe, K. Tsutsumi, N. Arai and K. Murata, Org. Lett. 2007, 9, 2565-2567. (g) M. Ito, Y. Endo and T. Ikariya, Organometallics 2008, 27, 6053-6055. (h) M. Ito, N. Tejima, M. Yamamura, Y. Endo and T. Ikariya, Organometallics, 2010, 29, 1886-1889. (i) M. Ito, Y. Endo, N. Tejima and T. Ikariya, Organometallics, 2010, 29, 2397-2399. (j) Z. M. Heiden and T. B. Rauchfuss, J. Am. Chem. Soc. 2009, 131, 3593-3600. (k) Z. M. Heiden and T. B. Rauchfuss, J. Am. Chem. Soc. 2006, 128, 13048-49. (l) Z.M. Heiden, B.J. Gorecki and T.B. Rauchfuss, Organometallics 2008, 27, 1542–1549. 5. (a) D. J. Cross, J. A. Kenny, I. Houson, L. Campbell, T. Walsgrove and M. Wills, Tetrahedron: Asymmetry 2001, 12, 1801-1806. (b) T. Hamada, T. Torii, K. Izawa, R. Noyori, T. Ikariya, Org. Lett. 2002, 4, 4373-4376. (c) T. Hamada, T. Torii, K. Izawa and T. Ikariya, Tetrahedron 2004, 60, 7411-7417. (d) T. Hamada, T. Torii, T. Onishi, K. Izawa and T. Ikariya, Org. Lett. 2004, 69, 7391-7394. (e) J. Wettergren, E. Buitrago, P. Ryberg and H. Adolfsson, Chem. Eur. J. 2009, 15, 5709-5718. (f) X. Wu, D. Vinci, T. Ikariya and J. Xiao, Chem. Commun. 2005, 4447-4449. (g) X. Wu, X. Li, A. Zanotti-Gerosa, A. Pettman, J. Liu, A. J. Mills and J. Xiao, Chem. Eur. J. 2008, 14, 2209-2222. (h) T. Thorpe, A. J. Blacker, S. M. Brown, C. Bubert, J. Crosby, S. Fitzjohn, J. P. Muxworthy and J. M. J. Williams, Tetrahedron Lett. 2001, 42, 4041-4043. (i) X. Wu, X. Li, F. King and J. Xiao, Angew. Chem. Int. Ed. 2005, 44, 3407-3411. (j) X. Wu and J. Xiao, Chem. Commun. 2007, 2449-2466. (k) D. Šterk, M. S. Stephan, B. Mohar, Tetrahedron: Asymmetry, 2002, 13, 2605-2608. (l) B. Mohar, M. Stephan and U. Urleb, Tetrahedron, 2010, 66, 4144-4149. (m) W. Baratta, F. Benedetti, A. Del Zotto, L. Fanfoni, F. Felluga, S. Magnolia, E. Putignano and P. Rigo, Organometallics 2010, 29, 3563-3570. (n) A. Schlatter, W.-D. Woggon, Adv. Synth. Catal. 2008, 350, 995-1000. (o) K. Ahlford, J. Ekström, A. B. Zaitsev, P. Ryberg and H. Adolfsson, Chem. Eur. J. 2009, 15, 11197-11209. (p) J. Soleimannejad, A. Sisson, C. White, Inorg. Chim. Acta. 2003, 352, 121-128. (q) T. J. Geldbech, P. J. Dyson, J. Am. Chem. Soc. 2004, 126, 8114-8115. 6. (a) H. Takamura, J. Ando, T. Abe, T. Murata, I. Kadota and D. Uemura, Tetrahedron Lett. 2008, 49, 4626-4629. (b) R. Fu, J. Chen, L.-C. Guo, J.-L. Ye, Y.-P. Ruan and P.-Q. Huang, Org. Lett. 2009, 11, 5242-5245. (c) G. Kumarasway, G. Ramakrishna, P. Naresh, B. Jagadeesh and B. Sridhar, J. Org. Chem. 2009, 74, 8468-8471. (d) B. Zhang, M.-H. Xu and G.-Q. Lin, Org. Chem. 2009, 11, 4712-4715. (e) M. Mogi, K. Fuji and M. Node, Tetrahedron: Asymmetry, 2004, 15, 3715-3717. (f) M. Hennig, K. Püntener and M. Scalone, Tetrahedron: Asymmetry, 2000, 11, 1849-1858. (g) P. A. Bradley, R. L. Carroll, Y. C. Lecouturier, R. Moore, P. Noeureuil, B. Patel, J. Snow and S. Wheeler, Org. Proc. Res. Dev. 2010, 14, 1326-1336. (h) Z. Ding, J. Yang, T. Wang, Z. Shen and Y. Zhang, Chem. Commun. 2009, 571-573. (i) B. Zhang, M.-H. Xu and G.-Q. Lin, Org. Lett. 2009, 11, 4712-4715. (j) Z. Liu, C. S. Schultz, C. A. Sherwood, S. Krska, P. G. Dormer, R. Desmond, C. Lee, E. C. Sherer, J. Shpungin, J. Cuff and F. Xu, Tetrahedron Lett. 2011, 52, 1685-1688. (k) I. Carpenter and M. L. Clarke, Synlett 2011, 65-68. (l) G. Kumaraswamy, G. Ramakrishna and B. Sridhar, Tetrahedron Lett. 2011, 52, 1778-1782. (m) Z. Geng, Y. Wu, S. Miao, Z. Shen and Y. Zhang, Tetrahedron Lett. 2011, 52, 907-909. (n) K. Leijondahl, A.-B. L. Fransson and J.-E. Bäckvall, J. Org. Chem. 2006, 71, 8622-8625. (o) N. J. Alcock, I. Mann, P. Peach and M. Wills, Tetrahedron: Asymmetry 2002, 13, 2485-2490. (p) N. J. Alcock, J. Hannedouche, D. J. Cross, J. A. Kenny, I. Mann, I. Houson, L. Campbell, T. Walsgrove and M. Wills, Tetrahedron 2006, 62, 1864-1876. (q) M. Miyagi, J. Takehara, S. Collet and K. Okano, Org. Process Res. Dev. 2000, 4, 346-348. (r) I. C. Lennon and J. A. Ramsden, Org. Process Res. Dev. 2005, 9, 110-112. (s) T. Kioke, K. Murata and T. Ikariya, Org. Lett. 2000, 2, 3833-3836. (t) K. Okano, K. Murata and T. Ikariya, Tetrahedron Lett. 2000, 41, 9277-9280. 7. (a) J. S. M. Samec, J.-E. Bäckvall, P. G. Andersson and P. Brandt, Chem. Soc. Rev. 2006, 35, 237–248. (b) P. Brandt, P. Roth, P. G. Andersson, J. Org. Chem. 2004, 69, 4885-4890. (c) J.-W. Handgraaf, E. J. Meijer, J. Am. Chem. Soc. 2007, 129, 3099-3103. (d) C. P. Casey, J. B. Johnson, J. Org. Chem. 2003, 68, 1998-2001. (e) M. Yamakawa, I. Yamada, R. Noyori, Angew. Chem. Int. Ed. 2001, 40, 2818-2821. (f) D. A. Alonso, P. Brandt, S. J. M. Nordin, P. G. Andersson, J. Am. Chem. Soc. 1999, 121, 9580-9588. (g) M. Yamakawa, H. Ito, R. Noyori, J. Am. Chem. Soc. 2000, 122, 1466-1478. (h) R. Noyori, M. Yamakawa, S. Hashiguchi, J. Org. Chem. 2001, 66, 7931-7944. 8. (a) A. M. Hayes, D. J. Morris, G. J. Clarkson and Wills, J. Am. Chem. Soc. 2005, 127, 7318–7319. (b) J. Hannedouche, G. J. Clarkson and M. Wills, J. Am. Chem. Soc. 2004, 126, 986–987. (c) F. K. Cheung, A. M. Hayes, D. J. Morris and M. Wills, Org. Biomol. Chem. 2007, 5, 1093-1103. (d) D. J. Morris, A. M. Hayes and M. Wills, J. Org. Chem. 2006, 71, 7035-7044. (e) F. K. Cheung, C. Lin, F. Minissi, A. Lorente Crivillé, M. A. Graham, D. J. Fox and M. Wills, Org. Lett. 2007, 9, 4659-4662. (f) F. K. Cheung, A. J. Clarke, G. J. Glarkson, D. J. Fox, M. A. Graham, C. Lin, A. Lorente Crivillé and M. Wills, Dalton Trans. 2010, 39, 1395–1402. (g) D. S. Matharu, D. J. Morris, A. M. Kawamoto, G. J. Clarkson and M. Wills, Org. Lett. 2005, 7, 5489-5491. (h) D. S. Matharu, J. E. D. Martins and M. Wills, Chem. Asian J. 2008, 3, 1374-1384. (i) R. Soni, F. K. Cheung, G. C. Clarkson, J. E. D. Martins, M. A. Graham and M. Wills, Org. Biomol. Chem. 2011, 9, 3290-3294. 9. Ikariya et al have recently prepared catalyst 5, through a different route to ours, and have evaluated it in asymmetric hydrogenation and transfer hydrogenation reactions: T. Touge, T. Hakamata, H. Nara, T. Kobayashi, N. Sayo, T. Saito, Y. Kayaki, and T. Ikariya, J. Am. Chem. Soc. 2011, 133, 14960–14963. 10. (a) J. E. D. Martins, G. J. Clarkson and M. Wills, Org. Lett. 2009, 11, 847 – 850. (b) J. E.D. Martins, M. A. Contreras Redondo and M. Wills, Tetrahedron: Asymmetry, 2010, 21, 2258-2264. 11. (a) D. Xue, Y.-C. Chen, X. Cui, Q.-W. Wang, J. Zhu and J.-G. Deng, J. Org. Chem. 2005, 70, 3584-3591. (b) T. Koike and T. Ikariya, Adv. Synth. Catal. 2004, 346, 37-41. (c) T. Koike and T. Ikariya, J. Organomet. Chem. 2007, 692, 408-419. (d) N. A. Cortez, R. Rodriguez-Apodaca, G. Aguirre, M. Parra-Hake, T. Cole, and R. Somanathan, Tetrahedron Lett. 2006, 47, 8515-8518. (e) N. A. Cortez, C. Z. Flores-Lopez, R. Rodriguez-Apodaca, L. Z. Flores-Lopez, M. Parra-Hake and R. Somanathan, R. ARKIVOC 2005, 6, 162-171.(f) W. J. Shan, F. C. Meng, Y. U. Wu, F. Mao and X. S. Li, J. Organomet. Chem. 2011, 696, 1687-1690. 12. (a) S. Gosiewska, R. Soni, G. J. Clarkson and M. Wills, Tetrahedron Lett. 2010, 51, 4214-4217. (b) V. Druais, M. J. Hall, C. Corsi, S. V. Wendeborn, C. Meyer and J. Cossy, Org. Lett. 2009, 11, 935-938. (c) J. Luo, H. Li, J. Wu, X. Xing and W.-M. Dai, Tetrahedron 2009, 65, 6828-6833. 13. (a) M. Wills in Modern Reduction Methods, ed. P. G. Andersson and I. J. Munslow, Wiley-VCH, Weinheim, 2008, Chapter 11, pp 271-296. (b) U. Uematsu, A. Fujii, S. Hasjiguchi, T. Ikariya and R. Noyori, J. Am. Chem. Soc. 1996, 118¸ 4916-4917. (c) G. D. Williams, C. E. Wade and M. Wills, Chem. Commun. 2005, 4735-4737. (d) J. Mao and D. C. Baker, Org. Lett., 1999, 1, 841-843. (e) J. Blacker and J. Martin, Scale up studies in Asymmetric Transfer Hydrogenation. In Asymmetric Catalysis on an Industrial Scale: Challenges, Approaches and Solutions; ed H. U. Blaser and E. Schmidt, Wiley, 2004, 201-216. (f) X. Sun, G. Manos, J. Blacker, J.; Martin and A. Gavriilidis, Org. Proc. Res. Dev. 2004, 8, 909-914. (g) D. Guijarro, O. Pablo and M. Yus, Tetrahedron Lett. 2009, 50, 5386-5388. (h) J. B. Åberg, J. S. M. Samec, J.-E. Bäckvall, Chem. Commun. 2006, 2771-2773. (i) C. P. Casey, T. B. Clark and I. A. Guzei, J. Am. Chem. Soc. 2007, 129, 11821-11827. (j) J. S. M. Samec, A. H. Éll, J. B. Åberg, T. Primalov, L. Eriksson and J.-E. Bäckvall, J. Am. Chem. Soc. 2006, 128, 14293-14305. (k) C. P. Casey and J. B. Johnson, J. Am. Chem. Soc. 2005, 127, 1883-1894. D. G. Blackmond, M. Ropic and M. Stefinovic, Organic Process Research & Development 2006, 10, 457 – 463. (l) G. D. Williams, R. A. Pike, C. E. Wade and M. Wills, Org. Lett. 2003, 5, 22, 4227 – 4230. (m) C. Wang, C.Li, X. Wu, A. Pettman and J. Xiao, Angew Chem. Int. Ed. 2009, 48, 6524-6528. (n) V. Parekh, J. A. Ramsden and M. Wills, Tetrahedron: Asymmetry, 2010, 21, 1549-1556. 14. (a) S. Shirai, H. Nara, Y. Kayaki and T. Ikariya, Organometallics, 2009, 28, 802-809. (b) C. Li and J. Xiao, J. Am. Chem. Soc. 2008, 130, 13208-13209. (c) C. Li, C. Wang, B. Villa-Marcos and J. Xiao, J. Am. Chem. Soc. 2008, 130, 14450-14451. (d) C. Li, B. Villa-Marcos and J. Xiao, J. Am. Chem. Soc. 2009, 131, 6967-6969. (e) T. Wang, L.-G. Zhuo, Z. Li, F. Chen, Z. Ding, Y. He, Q.-H. Fan, J. Xiang, Z.-X. Yu, A. S. C. Chan, J. Am. Chem. Soc. 2011, 133, 9878-9891. (f) H. Zhou, Z. Li, Z. Wang, T. Wang, L. Xu, Y. He, Q.-H. Fan, J. Pan, L. Gu and A. S. C. Chan, Angew Chem. Int. Ed. 2008, 47, 8464-8467. (g) Z-W. Li, T.-L. Wang, Y.-M. He, Z.-J. Wang, Q.-H. Fan, J. Pan and L.-J. Xu, Org. Lett. 2008, 10, 5265-5268. 15. D. A. Fletcher, R. F. McMeeking and D. Parkin, J. Chem. Inf. Comput. Sci. 1996, 36, 746-749.
URI: http://wrap.warwick.ac.uk/id/eprint/40371

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