From oblivion into the limelight: Iron (Domino) catalysis

Angewandte Chemie - International Edition

Volumn 48, Issue 8, 2009, Pages 1364-1367

  Furstner, Alois ^a  

^a MAX PLANCK INSTITUT FÜR KOHLENFORSCHUNG   (Germany)

Author keywords

catalysis; cross coupling; domino reactions; Grignard reagents; iron

Indexed keywords

REACTION KINETICS;

ARYL HALIDES; CROSS-COUPLING; CROSS-COUPLING REACTIONS; DOMINO REACTIONS; ELEMENTARY STEPS; GRIGNARD REAGENTS; IRON; IRON CATALYSIS; ONE-POT PROCEDURES; SCIENTIFIC COMMUNITIES; SLEEPING BEAUTIES;

CATALYSIS;

EID: 60149095698     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200805728     Document Type: Short Survey

References (50)

1. I. Bertini, H. B. Gray, S. J. Lippard, J. S. Valentine, Bioinorganic Chemistry, University Science Books, Mill Valley, 1994.
2. General reviews: a) C. Bolm, J. Legros, J. Le Paih, L. Zani, Chem. Rev. 2004, 104, 6217-6254;
3. b) Iron Catalysis in Organic Chemistry: Reactions and Applications (Ed.: B. Plietker), Wiley-VCH, Weinheim, 2008;
4. c) A. Furstner, R. Martin, Chem. Lett.2005, 34, 624-629.
5. W. M. Czaplik, M. Mayer, A. Jacobi von Wangelin, Angew. Chem. 2009, 121, 616-620;
6. Angew. Chem. Int. Ed. 2009, 48, 607-610.
7. M. S. Kharasch, O. Reinmuth, Grignard Reactions of Nonmetal-lic Substances, Constable, London, 1954.
8. B. Bogdanović, M. Schwickardi, Angew. Chem. 2000, 112, 4788-4790;
9. Angew. Chem. Int. Ed. 2000, 39, 4610-4612.
10. a) A. Furstner, A. Leitner, M. Méndez, H. Krause, J. Am. Chem. Soc. 2002, 124, 13856-13863;
11. b) A. Furstner, A. Leitner, Angew. Chem. 2002, 114, 632-635;
12. Angew. Chem. Int. Ed. 2002, 41, 609-612.
13. a) M. Tamura, J. K. Kochi, J. Am. Chem. Soc. 1971, 93, 1487-1489;
14. b) see also: G. Cahiez, H. Avedissian, Synthesis 1998, 1199-1205;
15. c) B. Scheiper, M. Bonnekessel, H. Krause, A. Furstner, J. Org. Chem. 2004, 69, 3943-3949.
16. A. Fürstner, A. Leitner, G. Seidel, Org. Synth. 2005, 81, 33-41.
17. A. Fürstner, A. Leitner, Angew. Chem. 2003, 115, 320-323;
18. Angew. Chem. Int. Ed. 2003, 42, 308-311.
19. Review: B. D. Sherry, A. Fürstner, Acc. Chem. Res. 2008, 41, 1500-1511.
20. a) M. Nakamura, K. Matsuo, S. Ito, E. Nakamura, J. Am. Chem. Soc. 2004, 126, 3686-3687;
21. b) T. Nagano, T. Hayashi, Org. Lett. 2004, 6, 1297-1299;
22. c) R. B. Bedford, D. W. Bruce, R. M. Frost, M. Hird, Chem. Commun. 2005, 4161-4163.
23. R. Martin, A. Fürstner, Angew. Chem. 2004, 116, 4045-4047;
24. Angew. Chem. Int. Ed. 2004, 43, 3955-3957.
25. A. C. Frisch, M. Beller, Angew. Chem. 2005, 117, 680-695;
26. Angew. Chem. Int. Ed. 2005, 44, 674-688.
27. A. Fürstner, H. Krause, C. W. Lehmann, Angew. Chem. 2006, 118, 454-458;
28. Angew. Chem. Int. Ed. 2006, 45, 440-444.
29. A. Fürstner, R. Martin, H. Krause, G. Seidel, R. Goddard, C. W. Lehmann, J. Am. Chem. Soc. 2008, 130, 8773-8787.
30. However, low conversions were observed when ester or cyano groups were present. These functional groups seem to inhibit the consumption of the magnesium, probably by surface deactiva-tion.
31. For recent advances in C-N, C-O, and C-S coupling, see: a) A. Correa, C. Bolm, Angew. Chem. 2007, 119, 9018-9021;
32. Angew. Chem. Int. Ed. 2007, 46, 8862-8865;
33. b) N. Xia, M. Taillefer, Chem. Eur. J. 2008, 14, 6037-6039;
34. c) A. Correa, M. Carril, C. Bolm, Angew. Chem. 2008, 120, 2922-2925;
35. Angew. Chem. Int. Ed. 2008, 47, 2880-2883.
36. S. Gaillard, J.-L. Renaud, ChemSusChem 2008, 1, 505-509.
37. A. Fürstner, K. Majima, R. Martín, H. Krause, E. Kattnig, R. Goddard, C. W. Lehmann, J. Am. Chem. Soc. 2008, 130, 1992-2004.
38. a) J. Norinder, A. Matsumoto, N. Yoshikai, E. Nakamura, J. Am. Chem. Soc. 2008, 130, 5858-5859;
39. b) J. Wen, J. Zhang, S.-Y. Chen, J. Li, X.-Q. Yu, Angew. Chem. 2008, 120, 9029-9032;
40. Angew. Chem. Int. Ed. 2008, 47, 8897-8900.
41. a) Y. Wang, E. A. F. Fordyce, F. Y. Chen, H. W. Lam, Angew. Chem. 2008, 120, 7460-7463;
42. Angew. Chem. Int. Ed. 2008, 47, 7350-7353;
43. b) S. Okada, K. Arayama, R. Murayama, T. Ishizuka, K. Hara, N. Hirone, T. Hata, H. Urabe, Angew. Chem. 2008, 120, 6966-6970;
44. Angew. Chem. Int. Ed. 2008, 47, 68606864;
45. c) Z. Lu, G. Chai, S. Ma, J. Am. Chem. Soc. 2007, 129, 14546-14547.
46. a) M. S. Chen, M. C. White, Science 2007, 318, 783-787;
47. b) P. D. Oldenburg, A. A. Shteinman, L. Que, Jr., J. Am. Chem. Soc. 2005, 127, 15672-15673;
48. c) F. G. Gelalcha, B. Bitterlich, G. Anilkumar, M. K. Tse, M. Beller, Angew. Chem. 2007, 119, 7431-7435;
49. Angew. Chem. Int. Ed. 2007, 46, 7293 -7296.
50. For an interesting case study, see: S. C. Bart, K. Chlopek, E. Bill, M. W. Bouwkamp, E. Lobkovsky, F. Neese, K. Wieghardt, P. J. Chirik, J. Am. Chem. Soc. 2006, 128, 13901-13912, and references therein.