On direct iron-catalyzed cross-coupling reactions

Pure and Applied Chemistry

Volumn 82, Issue 7, 2010, Pages 1545-1553

  Czaplik, Waldemar Maximilian ^a   Mayer, Matthias ^a   Grupe, Sabine ^a   Von Wangelin, Axel Jacobi ^a  

^a UNIVERSITY OF COLOGNE   (Germany)

Author keywords

Arylhalide; Catalysis; Cross coupling reactions; Grignard reaction; Iron

Indexed keywords

EID: 77954460314     PISSN: 00334545     EISSN: 13653075     Source Type: Journal    
DOI: 10.1351/PAC-CON-09-10-10     Document Type: Article

References (57)

1. (a) A. de Meijere, F. Diederich (Eds.). Metal-Catalyzed Cross-Coupling Reactions, Wiley-VCH, Weinheim (2004)
2. (b) M. Beller, C. Bolm (Eds.). Transition Metals for Organic Synthesis, Wiley- VCH, Weinheim (2004).
3. (a) Average world market prices in 2009: Pd (370 USD/oz), Ni (14.4 USD/lb); nickel toxicity: (b) L. Friberg, G. F. Nordberg, V. B. Vouk (Eds.). Handbook on the Toxicology of Metals, Elsevier, Amsterdam (1986)
4. (c) M. N. Hughes. Compreh. Coord. Chem. 6, 643 (1987)
5. (d) J. J. Hostynek, H. I. Maibach (Eds.). Nickel and the Skin: Absorption, Immunology, Epidemiology, and Metallurgy, CRC Press, Boca Raton (2002).
6. (a) C. Bolm, J. Legros, J. Le Paih, L. Zani. Chem. Rev. 104, 6217 (2004)
7. S. Enthaler, K. Junge, M. Beller. Angew. Chem., Int. Ed. 47, 3317 (2008)
8. (c) B. Plietker (Ed.). Iron Catalysis in Organic Chemistry, Wiley-VCH, Weinheim (2008)
9. (d) E. B. Bauer. Curr. Org. Chem. 12, 1341 (2008)
10. (e) W. M. Czaplik, M. Mayer, J. Cvengroš, A. Jacobi von Wangelin. ChemSusChem 2, 396 (2009).
11. M. S. Kharasch, E. K. Fields. J. Am. Chem. Soc. 63, 2316 (1941).
12. (a) M. Kumada, J. K. Kochi. J. Am. Chem. Soc. 93, 1487 (1971)
13. (b) J. K. Kochi. Acc. Chem. Res. 7, 351 (1974)
14. (c) J. K. Kochi, R. S. Smith. J. Org. Chem. 41, 502 (1976).
15. Selected examples: (a) A. Fürstner, A. Leitner. Angew. Chem., Int. Ed. 41, 609 (2002)
16. (b) A. Fürstner, A. Leitner, M. Méndez, H. Krause. J. Am. Chem. Soc. 124, 13856 (2002)
17. (c) A. Fürstner, A. Leitner. Angew. Chem., Int. Ed. 42, 308 (2003)
18. (d) A. Fürstner, D. De Souza, L. Parra-Rapado, J. T. Jensen. Angew. Chem., Int. Ed. 42, 5358 (2003)
19. (e) R. Martin, A. Fürstner. Angew. Chem., Int. Ed. 43, 3955 (2004)
20. (f) B. D. Sherry, A. Fürstner. Acc. Chem. Res. 41, 1500 (2008).
21. Selected examples: (a) G. Cahiez, H. Avedissian. Synthesis 1199 (1998)
22. (b) T. J. Korn, G. Cahiez, P. Knochel. Synlett 12, 1892 (2003)
23. (c) G. Cahiez, C. Chaboche, F. Mahuteau-Betzer, M. Ahr. Org. Lett. 7, 1943 (2005)
24. (d) G. Cahiez, C. Duplais, A. Moyeux. Org. Lett. 9, 3253 (2007)
25. (e) G. Cahiez, V. Habiak, C. Duplais, A. Moyeux. Angew. Chem., Int. Ed. 46, 4364 (2007)
26. (f) G. Cahiez, A. Moyeux, J. Buendia, C. Duplais. J. Am. Chem. Soc. 129, 13788 (2007).
27. Selected examples: (a) M. Nakamura, K. Matsuo, S. Ito, W. Nakamura. J. Am. Chem. Soc. 126, 3686 (2004)
28. (b) T. Hatakeyama, M. Nakamura. J. Am. Chem. Soc. 129, 9844 (2007)
29. (c) T. Hatakeyama, Y. Yoshimoto, T. Gabriel, M. Nakamura. Org. Lett. 10, 5341 (2008)
30. (d) T. Hatakeyama, S. Hashimoto, K. Ishizuka, M. Nakamura. J. Am. Chem. Soc. 131, 11949 (2009).
31. Selected examples: (a) T. Nagano, T. Hayashi. Org. Lett. 6, 1297 (2004)
32. (b) R. B. Bedford, D.W. Bruce, R. M. Frost, J. W. Goodby, M. Hird. Chem. Commun. 2822 (2004)
33. (c) C. Duplais, F. Bures, I. Sapountzis, T. J. Korn, G. Cahiez, P. Knochel. Angew. Chem., Int. Ed. 43, 2968 (2004)
34. (d) K. G. Dongol, H. Koh, M. Sau, C. L. L. Chai. Adv. Synth. Catal. 349, 1015 (2007)
35. (e) C. Kofink, B. Blank, S. Pagano, N. Götz, P. Knochel. Chem. Commun. 1954 (2007)
36. (f) J. Norinder, A. Matsumoto, N. Yoshikai, E. Nakamura. J. Am. Chem. Soc. 130, 5858 (2008)
37. (g) M. Carril, A. Correa, C. Bolm. Angew. Chem., Int. Ed. 47, 4862 (2008).
38. (a) J. L. Leazer, R. Cvetovich, F.-R. Tsay, U. Dolling, T. Vickery, D. Bachert. J. Org. Chem. 68, 3695 (2003)
39. (b) H. Kryk, G. Hessel, W. Schmitt. Org. Proc. Res. Dev. 11, 1135 (2007).
40. (a) Bond dissociation energies: Et-Br: 285 kJ/mol, Ph-Br: 335 kJ/mol, taken from: R. C. Weast, M. J. Astle (Eds.). CRC Handbook of Chemistry and Physics, CRC Press, Boca Raton (1981)
41. single electron transfer into the φ* orbital of the ArBr is reversible, and the φ*-σ* transition required for dissociation of the C-Br bond is slow
42. (c) reduction potentials Et-Br: -1.92 V, Ph-Br: -2.32 V, Mg2+: -2.37 V (SCE), taken from: G. S. Silverman. In Handbook of Grignard Reagents, G. S. Silverman, P. E. Rakita (Eds.), Chap. II.2, p. 9, CRC Press, Boca Raton (1996).
43. W. M. Czaplik, M. Mayer, A. Jacobi von Wangelin. Angew. Chem., Int. Ed. 48, 607 (2009).
44. (a) S. L. Buchwald, C. Bolm. Angew. Chem., Int. Ed. 48, 5586 (2009)
45. (b) P.-F. Larsson, A. Correa, M. Carril, P.-O. Norrby, C. Bolm. Angew. Chem., Int. Ed. 48, 5691 (2009).
46. W. M. Czaplik, M. Mayer, A. Jacobi von Wangelin. Synlett 2931 (2009).
47. F. Monnier, M. Taillefer. Angew. Chem., Int. Ed. 48, 6954 (2009).
48. B. Bogdanovič, M. Schwickardi. Angew. Chem., Int. Ed. 39, 4610 (2000).
49. (a) G. B. McVicker. Inorg. Chem. 14, 2087 (1975)
50. (b) L. E. Aleandri, B. Bogdanovič, P. Bons, C. Dürr, A. Gaidies, T. Hartwig, S. C. Huckett, M. Lagarden, U. Wilczok. Chem. Mater. 7, 1153 (1995)
51. (c) L. E. Aleandri, B. Bogdanovič, C. Dürr, S. C. Huckett, D. J. Jones, U. Kolb, M. Lagarden, J. Roziere, U. Wilczok. Chem.-Eur. J. 3, 1710 (1997)
52. (d) G. Siedlaczek, M. Schwickardi, U. Kolb, B. Bogdanovič, D. G. Blackmond. Catal. Lett. 55, 67 (1998).
53. In the absence of additives/ligands, the formation of nanoparticles has been observed: P.-H. Phua, L. Lefort, J. A. F. Boogers, M. Tristany, J. G. de Vries. Chem. Commun. 3747 (2009).
54. A. Fürstner, R. Martin, H. Krause, G. Seidel, R. Goddard, C. W. Lehmann. J. Am. Chem. Soc. 130, 8773 (2008).
55. D. Noda, Y. Sunada, T. Hatakeyama, M. Nakamura, H. Nagashima. J. Am. Chem. Soc. 131, 6078 (2009).
56. W. M. Czaplik, A. Jacobi von Wangelin, Unpublished results.
57. M. Amatore, C. Gosmini. Angew. Chem., Int. Ed. 47, 2089 (2008).