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Asymmetric catalysis using iron complexes : 'ruthenium lite'?

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Darwish, Moftah and Wills, Martin. (2012) Asymmetric catalysis using iron complexes : 'ruthenium lite'? Catalysis Science & Technology, Vol.2 (No.2). pp. 243-255. ISSN 2044-4753

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Official URL: http://dx.doi.org/10.1039/c1cy00390a

Abstract

A review of recent developments in the use of iron catalysts for asymmetric transformations, including hydrogenations, transfer hydrogenation, hydrosilylation and oxidation reactions.

Item Type:

Journal Article

Subjects:

Q Science > QD Chemistry

Divisions:

Faculty of Science > Chemistry

Library of Congress Subject Headings (LCSH):

Asymmetric synthesis, Iron catalysts

Journal or Publication Title:

Catalysis Science & Technology

Publisher:

Royal Society of Chemistry

ISSN:

2044-4753

Official Date:

2012

Dates:

Date	Event
2012	Published

Volume:

Vol.2

Number:

No.2

Page Range:

pp. 243-255

Identification Number:

10.1039/c1cy00390a

Status:

Peer Reviewed

Publication Status:

Published

Access rights to Published version:

Restricted or Subscription Access

Funder:

University of Warwick, Libya

References:

1) S. Enthaler, K. Junge and M. Beller, Angew. Chem. Int. Ed. 2008, 47, 3317-3321.
2) R. H. Morris, Chem. Soc. Rev. 2009, 38, 2282-2291.
3) R. M. Bullock, Angew. Chem. Int. Ed. 2007, 46, 7360-7363.
3) C.-L. Sun, B.i-J. Li, and Z.-J. Shi Chem. Rev. 2011, 111, 1293-1314.
4) (a) Iron Catalysis in Organic Chemistry: Reactions and Applications, Bernd Plietker (Editor), Wiley-VCH, Weinheim 2008. (b) Topics in Organometallic Chemistry, volume 33; Iron Catalysis; Fundamentals and Applications, Bernd Plietker (Editor), Springer, Heidelberg, 2011.
5) C. Bolm, J. legros, J. Le Paih and L. Zani, Chem. Rev. 2004, 104, 6217-6254.
6) A. Correa, O. Garcia Mancheno and C. Bolm, Chem. Soc. Rev. 2008, 37, 1108-1117.
7) S. Gaillard and J.-L. Renaud, ChemSusChem 2008, 1, 505-509.
8) K. Junge, K. Schröder and M. Beller, Chem. Commun. 2011, 47, 4849-4859.
9) G. Bauer and K. A. Kirchner, Angew. Chem. Int. Ed. 2011, 50, 5798-5800.
10) S. Chakraborty and H. Guan, Dalton Trans. 2010, 39, 7427-7436.
11) M. Costas, M.P. Mehn, M.P. Jensen and L. Que Jr, Chem. Rev. 2004, 104, 939-986.
12). R. Schlögl, Angew. Chem. Int. Ed. 2003, 42, 2004-2008
13) (a) C. Tard and C. J. Pickett, Chem. Rev. 2009, 109, 2245-2274. (b) J. A. Wright, P. J. Turrell and C. J. Pickett, Organometallics 2010, 29, 6146-6156. (c) M. J. Corr and J. A. Murphy, Chem. Soc. Rev. 2011, 40, 2279-2292. (d) M. L. Ghirardi, A. Dubini, J. Yu and P.-C. Maness, Chem. Soc. Rev. 2009, 38, 52-61.
14) (a) S. C. Bart, E. J. Hawrelak, E. Lobkovsky, and P. J. Chirik, Organometallics 2005, 24, 5518–5527. (b) S. C. Bart, E. Lobkovsky and P. J. Chirik J. Am. Chem. Soc. 2004, 126, 13794-13807. (c) A. M. Archer, M. W. Bouwkamp, M.-P. Cortez, E. Lobkovsky and P. J. Chirik, Organometallics 2006, 25, 4269-4278. (d) R. J. Trovitch, E. Lobkovsky and P. J. Chirik, Inorg. Chem. 2006, 45, 7252-7260. (e) R. J. Trovitch, E. Lobkovsky, E. Bill and P. J. Chirik, Organometallics 2008, 27, 1470–1478.
15) C. Sui-Seng, F. Freutel, A. J. Lough, R. H. Morris, Angew. Chem. Int. Ed. 2008, 47, 940-943.
16) (a) T. Li, R. Churlaud, A. J. Lough, K. Abdur-Rashid and R. H. Morris, Organometallics 2004, 23, 6239-6247. (b) V. Ruatenstrauch, X. Hoang-Cong, R. Churland, K. Abdur-Rashid and R. H. Morris, Chem; Eur. J. 2003, 9, 4954-4967. (c) C. A. Sandoval, T. Ohkuma, K. Muniz and R. Noyori, J. Am. Chem. Soc., 2003, 125, 13490-13503. (d) R. J. Hamilton and S. H. Bergens, J. Am. Chem. Soc. 2008, 130, 11979-11987. (e) J.-X. Gao, T. Ikariya and R. Noyori, Organometallics, 1996, 15, 1087-1089.
17) J.-S. Chen, L.-L. Chen, Y. Xing, G. Chen, W.-Y. Shen, Z.-R. Dong, Y.-Y. Li and J.-X. Gao, Acta. Chim. Sin. (Huaxue Xuebao), 2004, 62, 1745-1750.
18) A. A. Mikhailine, E. Kim, C. Dingels, A. J. Lough, R. H. Morris, Inorg. Chem. 2008, 47, 6587–6589.
19) A. Mikhailine, A. J. Lough, R. H. Morris, J. Am. Chem. Soc. 2009, 131, 1394–1395.
20) P. O. Lagaditis, A. A. Mikhailine, A. J. Lough, R. H. Morris, Inorg. Chem. 2010, 49, 1094-1102.
21) C. Sui-Seng, F. N. Haque, A. Hadzovic, A.-M. Pütz, V. Reuss, N. Meyer, A. J. Lough, M. Zimmer-De Iulii, R. H. Morris, Inorg. Chem. 2009, 48, 735-743.
22) R. H. Morris, Chem. Soc. Rev. 2009, 38, 2282-2291.
23) H.-Y. T. Chen, D. Di Tommaso, G. Hogarth and C. R. A. Catlow, Dalton Trans. 2011, 40, 402-411.
24) C. P. Casey and H. Guan, J. Am, Chem. Soc. 2007, 129, 5816-5817.
25) C. P. Casey and H. Guan, J. Am, Chem. Soc. 2009, 131, 2499-2507.
26) A. J. Pearson, R. J. Shively Jr. and R. A. Dubbert, Organometallics 1992, 11, 4096-4104.
27) H.-J. Knolker, E. Baum, H. Goesmann and R. Klauss, Angew. Chem. Int. Ed. 1999, 38, 2064-2066.
28) (a) B. L. Conley, M. K. Pennington-Boggio, E. Boz and T. J. Williams, T. J. Chem. Rev. 2010, 110, 2294-2312. (b) J. S. M. Samec, J.-E. Bäckvall, P. G. Andersson and P. Brandt, Chem. Soc. Rev. 2006, 35, 237-248. (c) S. E. Clapham A. Hadzovic and R. H. Morris, Coord. Chem. Rev. 2004, 248, 2201-2237. (d) C. P. Casey, S. W. Singer, D. R. Powell, R. K. Hayashi and M. Kavana, J. Am. Chem. Soc. 2001, 123, 1090-1100.
29) H. Zhang, D. Chen, Y. Zhang, G. Zhang and J. Liu, Dalton Trans. 2010, 39, 1972-1978.
30) S. Zhou, S. Fleischer, K. Junge and M. Beller, Angew. Chem. Int. Ed. 2011, 50, 5120-5124.
31) (a) A. Berkessel, S. Reichau, A. Von der Höh, N. Leconte and J.-M. Nordörfl, Organometallics 2011, 30, 3880-3887. (b) A. Berkessel and A. Van der Höh, ChemCatChem, 2011, 3, 861-867.
32) C. Bianchini, F. Farnetti, M. Graziani, M. Peruzzini and A. Polo, Organometallics 1993, 12, 3753-3761.
33) J. X. Gao, H. L. Wan, W. K. Wong, M. C. Tse and W. T. Wong, Polyhedron 1996, 15, 1241-1251.
34) N. Meyer, A. J. Lough, R. H. Morris, Chem. Eur. J. 2009, 15, 5605-5610.
35) A. A. Mikhailine and R. H. Morris, Inorg. Chem., 2010, 49, 11039–11044.
36) P. O. Lagaditis, A. J. Lough, and R. H. Morris, Inorg. Chem. 2010, 49, 10057–10066
37) P. O. Lagaditis, A. J. Lough and R. H. Morris, J. Am. Chem. Soc. 2011, 133, 9662-9665.
38) P. E. Sues, A. J. Lough and R. H. Morris, Organometallics 2011, 30, 4418-4431.
39) S. Zhou, S. Fleischer, K. Junge, S. Das, D. Addis and M. Beller, Angew. Chem. Int. Ed. 2010, 49, 8121-8125.
40) E. Weiss, R. G. Merenyi and W. Hubel, Chem. Ind. 1960, 407-408.
41) T. A. Shackleton, S. C. Mackie, S. B. Fergusson, L. J. Johnson and M. C. Baird, Organometallics 1990, 9, 2248-2253.
42) G. N. Schrauzer, J. Am. Chem. Soc. 1959, 81, 5307-5310.
43) M. K. Thorson, K. L. Klinkel, J. Wang and T. J. Williams, Eur. J. Inorg. Chem. 2009, 295-302.
44) M. G. Coleman, A. N. Brown, B. A. Bolton and H. Guan, Adv. Synth. Catal. 2010, 352, 967-970.
45) S. A. Moyer and T. W. Funk, Tetrahedron Lett. 2010, 51, 5430-5433.
46) (a) J. P. Hopewell, J. E. D. Martins, T. C. Johnson, J. Godfrey and M. Wills, Org. Biomol. Chem. 2011, 9, in press. (b) T. C. Johnson, G. J. Clarkson and M. Wills, Organometallics 2011, 30, 1859-1868.
47) S. Enthaler, B. Hagemann, G. Erre, K. Junge and M. Beller, Chem. Asian J. 2006, 1, 598-604.
48) (a) S. Enthaler, B. Spilker, G. Erre, K.Junge, M. K. Tse and M. Beller, Tetrahedron 2008, 64, 3867-3876. (b) S. Enthaler, G. Erre, M. K. Tse, K. Junge and M. Beller, Tetrahedron Lett. 2006, 47, 8095-8099.
49) A. Buchard, H. Heuclin, A. Auffrant, X. F. Le Goff and P. Le Floch, Dalton Trans. 2009, 38, 1659-1667.
50) A. Naik, T. Maji and O. Reiser, Chem. Commun. 2010, 46, 4475-4477.
51) (a) H. Brunner, R. Eder, B. Hammer and U. Klement, J. Organomet. Chem. 1990, 394, 555-567. (b) T. Muraoka, Y. Shimizu, H. Kobayashi, K. Ueno and H. Ogino, Organometallics 2010, 29, 5423-5426. (c) D. V. Gutsulyak, L. G. Kuzmina, J. A. K. Howard, S. F. Vyboishchikov and G. I. Nikonov, J. Am. Chem. Soc. 2008, 130, 3732-3733. (d) P. Bhattaccharya, J. A. Krause and H. Guan, Organometallics 2011, 30, 4720-4729.
52) H. Nishiyama and A. Furuta, Chem. Commun 2007, 760-762.
53) T. Inagaki, L. T. Phong, A. Furuta, J.-I. Ito and H. Nishiyama, Chem. Eur. J. 2010, 16, 3090-96.
54) T. Inagaki, A. Ito, J.-I. Ito and H. Nishiyama Angew. Chem. Int. Ed. 2010, 49, 9384-9387.
55) S. Hosokawa, J.-I. Ito and H. Nishiyama, Organometallics 2010, 29, 5773-5775.
56) (a) A. M. Tondreau, J. M. Darmon, B. M. Wile, S. K. Floyd, E. Lobkovsky and P. J. Chirik, Organometallics 2009, 28, 3928-3940. (b) A. M. Tondreau, E. Lobkovsky and P. J. Chirik, Org. Lett. 2008, 10, 2789-2792.

57) (a) N. S. Shaikh, S. Enthaler, K. Junge and M. Beller, Angew. Chem. Int. Ed. 2008, 47, 2497-2501. (b) N. S. Shaikh, K. Junge and M. Beller, Org. Lett. 2007, 9, 5429-5432. (c) D. Addis, N. Shaikh, S. Zhou, S. Das, K. Junge and M. Beller, Chem: Asian J. 2010, 5, 1687-1691.
58) B. K. Langlotz, H. Wadepohl and L. H. Gade, Angew. Chem. Int. Ed. 2008, 47, 4670-4674.
59) J. P. Collman, Z. Wang, A. Straumanis and M. Quelquejeu, J. Am. Chem.Soc. 1999, 121, 460-461.
60) E. Rose, Q.-Z. Ren and B. Andrioletti, Chem. Eur. J. 2004, 10, 224-230.
61) E. Rose, B. Andrioletti, S. Zrig and M. Quelquejeu-Ethève, Chem. Soc. Rev. 2011, 34, 573-583.
62) M. B. Francis and E. N. Jacobsen, Angew. Chem. Int. Ed. 1999, 38, 937-941.
63) Q. F. Cheng, X. Y. Xu, W. X. Ma, S. J. Yang and T. P. You, Chin. Chem. Lett. 2005, 16, 1467-1470.
64) (a) K. Schröder, X. Tong, B. Bitterlich, M. K. Tse, F. G. Gelalcha, A. Brückner and M. Beller, Tetrahedron Lett. 2007, 48, 6339-6342. (b) G. Anilkumar, B. Bitterlich, F. G. Gelalcha, M. K. Tse and M. Beller, Chem. Commun. 2007, 289-291.
65) F. G. Gelalcha, B. Bitterlich, G. Anilkumar, M. K. Tse and M. Beller, Angew. Chem. Int. Ed. 2007, 46, 7293-7296.
66) F. G. Gelalcha, G. Anilkumar, M. K. Tse, A Brückner and M. Beller,Chem. Eur. J. 2008, 14, 7687-7698.
67) M. C. White, A. G. Doyle and E. N. Jacobsen, J. Am. Chem. Soc. 2001, 123, 7194-7195.
68) C. Marchi-Delapierre, A. Jorge-Robin, A. Thibon and S. Ménage, Chem. Commun. 2007, 1166-1168.
69) H.-L. Yeung, K.-C. Sham, C.-S. Tsang, T.-C. Lau and H.-L. Kwong, Chem. Commun. 2008, 3801-3803.
70) Y. Nishikawa and H. Yamamoto, J. Am. Chem. Soc. 2011, 133, 8432-8435.
71) (a) M. R. Bukowski, P. Comba, A. Lienke, C. Limberg, C. Lopez de Laorden, R. Mas-Ballesté, M. Merz and L. Que Jr. Angew. Chem. Int. Ed. 2006, 45, 3446–3449. (b) P. D. Oldenburg, A. A. Shteinman and L. Que Jr. J. Am. Chem. Soc. 2005, 127, 15672-15673. (c) E. J. Klinker, T. A. Jackson, M. P. Jensen, A. Stubna, G. Juhasz, E. L. Bominaar, E. Munck and L. Que Jr. Angew. Chem. Int. Ed. 2006, 45, 7394- 7397.
72) K. Suzuki, P. D. Oldenburg and L. Que Jr. Angew. Chem. Int. Ed. 2008, 47, 1887-1889.
73) L.-C. Chiang, K. Konishi, T. Aida and S. Inoue, J. Chem. Soc. Chem. Commun.1992, 254-256.
74) J. Legros and C. Bolm, Angew. Chem. Int. Ed. 2003, 42, 5487-5489.
75) (a) J. Legros and C. Bolm, Angew. Chem. Int. Ed. 2004, 43, 4225-4228. (b) J. Legros and C. Bolm, Chem. Eur. J. 2005, 11, 1086-1092 (c) A. Krote, J. Legros and C. Bolm, Synlett 2004, 2397-2399.
76) K. P. Bryliakov and E.P. Talsi, Angew. Chem. Int. Ed. 2004, 43, 5228-5230.
77) H. Egami and T. Katsuki, J. Am. Chem. Soc. 2007, 129, 8940-8941.
78) T. Kunisu, T. Oguma and T. Katsuki, J. Am. Chem. Soc. 2011, 133, 12937-12939.
79) H. Egami and T. Katsuki, J. Am. Chem. Soc. 2009 131, 6082-6083.
80) H. Egami, K. Matsumoto, T. Oguma, T. Kunisu and T. Katsuki, J. Am. Chem. Soc. 2010 132, 13633-13635.
81) S.-F. Zhu, Y. Cai, H.-X. Mao, J.-H. Xie and Q.-L. Zhou, Nature Chemistry 2010, 2, 546-551.
82) M. Kawatsura, Y. Komatsu, M. Yamamoto, S. Hayase and T. Itoh, Tetrahedron Lett. 2007, 48, 6480-6482.
83) M. Nakamura, A. Hirai, and E. Nakamura, J. Am. Chem. Soc. 2000, 122, 978-979.
84) (a) S. Kanemasa, Y. Oderaotoshi, H. Yamamoto, J. Tanaka and E. Wada, J. Org. Chem. 1997, 62, 6454-6455 (b) S. Kanemasa, Y. Oderaotoshi, S.-I. Sakaguchi, H. Yamamoto J. Tanaka, E. Wada and D. P. Curran, J. Am. Chem. Soc. 1998, 120, 3074. (c) E. J. Corey and K. Ishihara, Tetrahedron Lett. 1992, 33, 6807-6810. (d) E. J. Corey, N. Imai and H.-Y. Zhang, J. Am. Chem. Soc. 1991, 113, 728 – 729. (e) N. Khiar, I.Fernandez and F. Alcudia, Tetrahedron Lett. 1993, 34, 123-126. (f) S. Matsukawa, H. Sugama and T. Imamoto, Tetrahedron Lett. 2000, 41, 6461-6465.
85) (a) E. P. Kündig, B. Bourdin and G. Bernardinelli, Angew. Chem. Int. Ed. 1994, 33, 1856-1858. (b) M. E. Bruin and E. P. Kündig, Chem. Commun.1998, 2635-2636.
86) (a) J. Christoffers, A. Mann and J. Pickardt, Tetrahedron 1999, 55, 5377-5388. (b) J. Christoffers and U. Röβler, Tetrahedron: Asymmetry 1999, 10, 1207 – 1215. (c) J. Christoffers, and A. Mann, Eur. J. Org. Chem. 1999, 1475-1479.
87) (a) H. T. Dieck and J. Dietrich, Chem. Ber. 1984, 117, 694-701. (b) H. T. Dieck and J. Dietrich, Angew. Chem., Int. Ed. Engl. 1985, 24, 781-783. (c) L. Eberson, B. Olofsson and J. O. Svensson, Acta Chem. Scand. 1992, 46, 1005-1015. (d) A. Greco, A. Carbonaro and G. Dall’Asta, J. Org. Chem. 1970, 35, 271-274.
88) K. U. Baldenius, H. T. Dieck, W. A. König, D. Icheln and T. Runge, Angew. Chem., Int. Ed. Engl. 1992, 31, 305-307.
89) (a) K. S. Williamson and T. P. Yoon, J. Am. Chem. Soc. 2010, 132, 4570-4571. (b) S. Hong, Y.-M. Lee, W. Shin, S. Fukuzumi and W. Nam, J. Am. Chem. Soc. 2009, 131, 13910-13911. (c) A. S. Ionkin, W. J. Marshall, D. J. Adelman, B. B. Fones, B. M. Fish and M. F. Schiffhauer, Organometallics 2008, 27, 1902-1911. (d) B. Anxionnat, A. Guerinot, S. Reymond and J. Cossy, Tetrahedron Lett. 2009, 50, 3470-3473. Quite interesting. (e) J. G. Liu, T. Ohta, S. Yamaguchi, T. Ogura, S. Sakamoto, Y. Maeda and Y. Naruta, Angew. Chem.Int. Ed. 2009, 48, 9262-9267. (f) O. G. Mancheno, Angew. Chem. Int. Ed. 2011, 50, 2216-2218. (g) K. Iwanami, K. Yano and T. Oriyama, Chem. Lett. 2007, 36, 38-39. (h) M. D. Bhor, M. J. Bhanushali, N. S. Nandurkar and B. M. Bhanage, Tetrahedron Lett. 2008, 49, 965-969. (i) V. Polshin, D.-L. Popescu, A. Fischer, A. Chanda, D. C. Horner, E. S. Beach, J. Henry, Y.-L. Qian, C. P. Horwitz, G. Lente, I. Fabian, E. Münck, E. L. Bominaar, A. D. Ryabov, and T. J. Collins, J. Am. Chem. Soc. 2008, 130, 4497–4506.
90) A. Fürstner, K. Majima, R. Martín, H. Krause, E. Kattnig, R. Goddard and C. W. Lehmann, J. Am. Chem. Soc. 2008, 130, 1992–2004.
91) (a) L. E. N. Allan, M. P. Shaver, A. J. P. White and V. C. Gibson, Inorg. Chem. 2007, 46, 8963–8970. (b) F. A. R. Kaul, G. T. Puchta, G. D. Frey, E. Herdtweck, and W. A. Herrmann, Organometallics 2007, 26, 988–999.
92) M. S. Chen and M. C. White, Science 2007, 318, 783-787. M. S. Chen and M. C. White, Science 2010, 327, 566-571.
93) (a) E. J. Daida and J. C. Peters, Inorg. Chem. 2004, 43, 7474–7485. (b) V. Kandepi. J. M. S. Cardoso, E. Peris and B. Royo, Organometallics 2010, 29, 2777-2782. (c) F. Jiang, D. Bezier, J.-B. Sortais and C. Darcel, Adv. Synth. Catal. 2011, 353, 239-244. (d) R. Langer, G. Leitus, Y. Ben-David, and D. Milstein, Angew. Chem. Int. Ed. 2011, 50, 2120-2124.