Catalytic properties of low oxidation state iron complexes in cross-coupling reactions: Anthracene iron(-I) complexes as competent catalysts

ChemCatChem

Volumn 3, Issue 10, 2011, Pages 1572-1577

  Weber, Katharina ^a   Schnöckelborg, Eva Maria ^a   Wolf, Robert ^a,b  

^a UNIVERSITY OF MÜNSTER   (Germany)

^b UNIVERSITY OF REGENSBURG   (Germany)

Author keywords

Catalysis; Cross couplings; Iron; Reaction mechanisms

Indexed keywords

EID: 80053584879     PISSN: 18673880     EISSN: 18673899     Source Type: Journal    
DOI: 10.1002/cctc.201100199     Document Type: Article

References (95)

1. Handbook of Organopalladium Chemistry for Organic Synthesis (Ed.: E. Negishi), Wiley, New York, 2002;
2. J. Tsuji, Palladium Reagents and Catalysts, Wiley, Chichester, 2004;
3. Metal-Catalyzed Cross-coupling reactions (Eds.: A. deMeijere, F. Diederich), Wiley-VCH, Weinheim, 2004;
4. Transition Metals for Organic Synthesis (Eds.: M. Beller, C. Bolm), Wiley-VCH, Weinheim, 2004.
5. For a series of reviews on transition metal-catalyzed cross couplings see the following collection of reviews: J. Organomet. Chem. 2002, 653, 1-303.
6. M. Tamura, J. K. Kochi, J. Am. Chem. Soc. 1971, 93, 1487;
7. J. K. Kochi, Acc. Chem. Res. 1974, 7, 351;
8. S. M. Neumann, J. K. Kochi, J. Org. Chem. 1975, 40, 599;
9. J. S. Smith, J. K. Kochi, J. Org. Chem. 1976, 41, 502;
10. J. K. Kochi, J. Organomet. Chem. 2002, 653, 11.
11. Reviews:
12. C. Bolm, J. Legros, J. LePaih, L. Zani, Chem. Rev. 2004, 104, 6217;
13. H. Shinokubo, K. Oshima, Eur. J. Org. Chem. 2004, 2071;
14. A. Fürstner, R. Martin, Chem. Lett. 2005, 34, 624;
15. B. D. Sherry, A. Fürstner, Acc. Chem. Res. 2008, 41, 1500;
16. G. Cahiez, C. Duplais in The Chemistry of Organomagnesium Compounds (Eds.: Z. Rappoport, I. Marek), Wiley-VCH, Weinheim. 2008, ch.13, p.595;
17. A. Leitner in Iron Catalysis in Organic Synthesis (Ed.: B. Plietker), Wiley-VCH, Weinheim, 2008, 147;
18. A. Correa, O. G. Mancheño, C. Bolm, Chem. Soc. Rev. 2008, 37, 1108;
19. W. M. Czaplik, M. Mayer, J. Cvengroš, A. JacobivonWangelin, ChemSusChem 2009, 2, 396;
20. A. Fürstner, Angew. Chem. 2009, 121, 1390; Angew. Chem. Int. Ed. 2009, 48, 1364;
21. E. Nakamura, Y. Nohiko, J. Org. Chem. 2010, 75, 6061.
22. Couplings of aryl electrophiles:
23. A. Fürstner, A. Leitner, M. Méndez, H. Krause, J. Am. Chem. Soc. 2002, 124, 13856;
24. A. Fürstner, A. Leitner, Angew. Chem. 2002, 114, 632; Angew. Chem. Int. Ed. 2002, 41, 609;
25. J. Quintin, X. Franck, R. Hocquemiller, B. Figadére, Tetrahedron Lett. 2002, 43, 3547;
26. G. Seidel, D. Laurich, A. Fürstner, J. Org. Chem. 2004, 69, 3950;
27. B. Scheiper, M. Bonnekessel, H. Krause, A. Fürstner, J. Org. Chem. 2004, 69, 3943;
28. I. Sapountzis, W. Lin, C. C. Kofink, C. Despotopoulou, P. Knochel, Angew. Chem. 2005, 117, 1682; Angew. Chem. Int. Ed. 2005, 44, 1654;
29. T. Hatakeyama, M. Nakamura, J. Am. Chem. Soc. 2007, 129, 9844;
30. C. C. Kofink, B. Blank, S. Pagano, N. Goetz, P. Knochel, Chem. Commun. 2007, 1954;
31. K. Ding, F. Zannat, J. C. Morris, W. W. Brennessel, P. L. Holland, J. Organomet. Chem. 2009, 694, 4204.
32. Couplings of alkyl electrophiles:
33. T. Nagano, T. Hayashi, Org. Lett. 2004, 6, 1297;
34. R. B. Bedford, D. W. Bruce, R. M. Frost, J. W. Goodby, M. Hird, Chem. Commun. 2004, 2822;
35. R. Martin, A. Fürstner, Angew. Chem. 2004, 116, 4045; Angew. Chem. Int. Ed. 2004, 43, 3955;
36. M. Nakamura, K. Matsuo, S. Ito, E. Nakamura, J. Am. Chem. Soc. 2004, 126, 3686;
37. R. B. Bedford, D. W. Bruce, R. M. Frost, M. Hird, Chem. Commun. 2005, 4161;
38. M. Nakamura, S. Ito, K. Matsuo, E. Nakamura, Synlett 2005, 1794;
39. R. B. Bedford, M. Betham, D. W. Bruce, A. A. Danopoulos, R. M. Frost, M. Hird, J. Org. Chem. 2006, 71, 1104;
40. G. Cahiez, C. Duplais, A. Moyeux, Org. Lett. 2007, 9, 3253;
41. G. Cahiez, V. Habiak, C. Duplais, A. Moyeux, Angew. Chem. 2007, 119, 4442; Angew. Chem. Int. Ed. 2007, 46, 4364;
42. K. G. Dongol, H. Koh, M. Sau, C. L. L. Chai, Adv. Synth. Catal. 2007, 349, 1015;
43. A. Guérinot, S. Reymond, J. Cossy, Angew. Chem. 2007, 119, 6641; Angew. Chem. Int. Ed. 2007, 46, 6521;
44. R. R. Chowdhury, A. K. Crane, C. Fowler, P. Kwong, C. M. Kozak, Chem. Commun. 2008, 94;
45. S. Ito, Y. Fujiwara, E. Nakamura, M. Nakamura, Org. Lett. 2009, 11, 4306;
46. X. Quia, L. N. Dawe, C. M. Kozak, Dalton Trans. 2010, 40, 933;
47. H. Gao, C. Yan, X. Tao, Y. Xia, H. Sun, Q. Shen, Y. Zhang, Organometallics 2010, 29, 4189;
48. S. Kawamura, K. Ishizuka, H. Takaya, M. Nakamura, Chem. Commun. 2010, 46, 6054;
49. A. M. Reckling, D. Martin, L. N. Dawe, A. Decken, C. M. Kozak, J. Organomet. Chem. 2011, 696, 787;
50. F. Xue, J. Zhao, T.S.A. Hor, Dalton Trans. DOI:.
51. Couplings of alkenyl electrophiles:
52. G. Cahiez, S. Marquais, Tetrahedron Lett. 1996, 37, 1773;
53. G. Cahiez, S. Marquais, Pure Appl. Chem. 1996, 68, 53;
54. G. Cahiez, H. Avedissian, Synthesis 1998, 1199;
55. W. Dohle, F. Kopp, G. Cahiez, P. Knochel, Synlett 2001, 1901;
56. M. Dos Santos, X. Franck, R. Hocquemiller, B. Figadére, J.-F. Peyrat, O. Provot, J.-D. Brion, M. Alami, Synlett 2004, 2697;
57. G. Dunet, P. Knochel, Synlett 2006, 407;
58. G. Cahiez, V. Habiak, O. Gager, Org. Lett. 2008, 10, 2389;
59. G. Cahiez, O. Gager, V. Habiak, Synthesis 2008, 2636;
60. T. Hatakeyama, N. Nakagawa, M. Nakamura, Org. Lett. 2009, 11, 4496;
61. H. Nishikado, H. Nakatsuji, K. Ueno, R, Nagase, Y. Tanabe, Synlett 2010, 2002.
62. Couplings of acyl and imidoyl electrophiles:
63. C. Duplais, F. Bures, T. Korn, I. Sapountzis, G. Cahiez, P. Knochel, Angew. Chem. 2004, 116, 3028; Angew. Chem. Int. Ed. 2004, 43, 2968;
64. L. K. Ottesen, F. Ek, R. Olsson, Org. Lett. 2006, 8, 1771.
65. Homocouplings:
66. T. Nagano, T. Hayashi, Org. Lett. 2005, 7, 4161;
67. G. Cahiez, C. Chaboche, F. Mahuteau-Betzer, M. Ahr, Org. Lett. 2005, 7, 1943;
68. G. Cahiez, L. Foulgoc, A. Moyeux, Angew. Chem. 2009, 121, 3013; Angew. Chem. Int. Ed. 2009, 48, 2969;
69. X. Xu, D. Cheng, W. Pei, J. Org. Chem. 2006, 71, 6637;
70. Y.-Y. Zhang, J.-D. Lin, X.-L. Xu, J.-H. Li, Synth. Commun. 2010, 40, 2556.
71. Direct Cross Couplings:
72. W. M. Czaplik, M. Mayer, A. Jacobi von Wangelin, Angew. Chem. 2009, 121, 616; Angew. Chem. Int. Ed. 2009, 48, 607;
73. W. M. Czaplik, M. Mayer, A. Jacobi von Wangelin, ChemCatChem 2011, 3, 135;
74. W. M. Czaplik, M. Mayer, S. Grupe, A. JacobivonWangelin, Pure Appl. Chem. 2010, 82, 1545.
75. S. Enthaler, K. Junge, M. Beller, Angew. Chem. 2008, 120, 3363-3367; Angew. Chem. Int. Ed. 2008, 47, 3317-3321;
76. Iron Catalysis in Organic Synthesis (Ed.: B. Plietker), Wiley-VCH, Weinheim, 2008.
77. A. Fürstner, R. Martin, H. Krause, G. Seidel, G. Goddard, C. W. Lehmann, J. Am. Chem. Soc. 2008, 130, 8773;
78. J. Kleimark, A. Hedström, P.-F. Larsson, C. Johansson, P.-O. Norrby, ChemCatChem 2009, 1, 152;
79. D. Noda, Y. Sunada, T. Hatakeyama, M. Nakamura, H. Nagashima, J. Am. Chem. Soc. 2009, 131, 6078;
80. T. Hatakeyama, S. Hashimoto, K. Ishizuka, M. Nakamura, J. Am. Chem. Soc. 2009, 131, 11949.
81. L. E. Aleandri, B. Bogdanović, P. Bons, C. Duerr, A. Gaidies, T. Hartwig, S. C. Huckett, M. Lagarden, U. Wilczok, R. A. Brand, Chem. Mater. 1995, 7, 1153;
82. B. Bogdanović, M. Schwickardi, Angew. Chem. 2000, 112, 4788; Angew. Chem. Int. Ed. 2000, 39, 4610.
83. O. García-Mancheño, Angew. Chem. 2011, 123, 2264; Angew. Chem. Int. Ed. 2011, 50, 2216.
84. W. W. Brennessel, R. E. Jilek, J. E. Ellis, Angew. Chem. 2007, 119, 6244; Angew. Chem. Int. Ed. 2007, 46, 6132;
85. R. Wolf, N. Ghavtadze, K. Weber, E.-M. Schnöckelborg, B. deBruin, A. W. Ehlers, K. Lammertsma, Dalton Trans. 2010, 39, 1453;
86. S. D. Ittel, C. A. Tolman, Organometallics 1982, 1, 1432;
87. R. Wolf, E.-M. Schnöckelborg, Chem. Commun. 2010, 46, 2832;
88. E.-M. Schnöckelborg, R. Wolf, unpublished results;
89. H. Felkin, P. J. Knowles, B. Meunier, A. Mitschler, L. Ricard, R. Weiss, J. Chem. Soc. Chem. Commun. 1974, 44;
90. M. J. Mays, P. L. Sears, J. Chem. Soc. Dalton Trans. 1973, 1873.
91. [12a]
92. R. Wolf, J. C. Slootweg, A. W. Ehlers, F. Hartl, B. deBruin, M. Lutz, A. L. Spek, K. Lammertsma, Angew. Chem. 2009, 121, 3150; Angew. Chem. Int. Ed. 2009, 48, 3104;
93. R. Wolf, A. W. Ehlers, M. M. Khusniyarov, F. Hartl, B. deBruin, G. J. Long, F. Grandjean, F. M. Schappacher, R. Pöttgen, J. C. Slootweg, M. Lutz, A. L. Spek, K. Lammertsma, Chem. Eur. J. 2010, 16, 14322.
94. [6f, 12c] In this context, it should be noted that the anthracene ligands of complexes 1 and 2 have significant radical character, which could trigger single-electron transfer processes. Radical processes could also be involved in the formation of the catalytically active species from the catalyst precursors. Although we did not observe the formation of by-products originating from radical intermediates in significant quantities, the formation of short-lived radical intermediates thus cannot be excluded at present.
95. [12b]