Cross-coupling of alkyl halides with aryl Grignard reagents catalyzed by a low-valent iron complex

Angewandte Chemie - International Edition

Volumn 43, Issue 30, 2004, Pages 3955-3957

  Martin, Rubén ^a   Fürstner, Alois ^a  

^a MAX PLANCK INSTITUT FÜR KOHLENFORSCHUNG   (Germany)

Author keywords

Alkyl halides; Cross coupling; Grignard reagents; Iron

Indexed keywords

CATALYSIS; CATALYSTS; IRON COMPOUNDS;

ALKYL HALIDES; CROSS COUPLING REACTIONS; GRIGNARD REAGENTS;

HALOGEN COMPOUNDS;

ALKYL GROUP; HALIDE; IRON COMPLEX; IRON DERIVATIVE; MAGNESIUM DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; REAGENT;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CROSS COUPLING REACTION; GRIGNARD REACTION;

EID: 4544294922     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200460504     Document Type: Article

References (65)

1. Metal-Catalyzed Cross-Coupling Reactions (Eds.: F. Diederich, P. J. Stang), Wiley-VCH, Weinheim, 1998.
2. For pertinent discussions see: a) D. J. Cárdenas, Angew. Chem. 2003, 115, 398-401; Angew. Chem. Int. Ed. 2003, 42, 384-387;
3. For pertinent discussions see: a) D. J. Cárdenas, Angew. Chem. 2003, 115, 398-401; Angew. Chem. Int. Ed. 2003, 42, 384-387;
4. b) T.-Y. Luh, M. Leung, K.-T. Wong, Chem. Rev. 2000, 100, 3187-3204.
5. T. Ishiyama, S. Abe, N. Miyaura, A. Suzuki, Chem. Lett. 1992, 691-694.
6. a) A. Devasagayaraj, T. Stüdemann, P. Knochel, Angew. Chem. 1995, 107, 2952-2954; Angew. Chem. Int. Ed. Engl. 1995, 34, 2723-2725;
7. a) A. Devasagayaraj, T. Stüdemann, P. Knochel, Angew. Chem. 1995, 107, 2952-2954; Angew. Chem. Int. Ed. Engl. 1995, 34, 2723-2725;
8. b) R. Giovannini, P. Knochel, J. Am. Chem. Soc. 1998, 120, 11 186-11 187;
9. c) R. Giovannini, T. Stüdemann, A. Devasagayaraj, G. Dussin, P. Knochel, J. Org. Chem. 1999, 64, 3544-3553;
10. d) M. Piber, A. E. Jensen, M. Rottländer, P. Knochel, Org. Lett. 1999, 1, 1323-1326;
11. ) A. E. Jensen, P. Knochel, J. Org. Chem. 2002, 67, 79-85.
12. a) J. Zhou, G. C. Fu, J. Am. Chem. Soc. 2004, 126, 1340-1341;
13. b) M. R. Netherton, C. Dai, K. Neuschütz, G. C. Fu, J. Am. Chem. Soc. 2001, 123, 10 099-10 100;
14. c) J. H. Kirchhoff, M. R. Netherton, I. D. Hills, G. C. Fu, J. Am. Chem. Soc. 2002, 124, 13 662-13 663;
15. d) M. R. Netherton, G. C. Fu, Angew. Chem. 2002, 114, 4066-4068; Angew. Chem. Int. Ed. 2002, 41, 3910-3912;
16. d) M. R. Netherton, G. C. Fu, Angew. Chem. 2002, 114, 4066-4068; Angew. Chem. Int. Ed. 2002, 41, 3910-3912;
17. e) J. Zhou, G. C. Fu, J. Am. Chem. Soc. 2003, 125, 12 527-12 530;
18. f) J. Zhou, G. C. Fu, J. Am. Chem. Soc. 2003, 125, 14 726-14 727;
19. g) H. Tang, K. Menzel, G. C. Fu, Angew. Chem. 2003, 115, 5233-5236; Angew. Chem. Int. Ed. 2003, 42, 5079-5082.
20. g) H. Tang, K. Menzel, G. C. Fu, Angew. Chem. 2003, 115, 5233-5236; Angew. Chem. Int. Ed. 2003, 42, 5079-5082.
21. a) J. Terao, H. Watanabe, A. Ikumi, H. Kuniyasu, N. Kambe, J. Am. Chem. Soc. 2002, 124, 4222-4223;
22. b) J. Terao, Y. Naitoh, H. Kuniyasu, N. Kambe, Chem. Lett. 2003, 32, 890-891;
23. c) J. Terao, A. Ikumi, H. Kuniyasu, N. Kambe, J. Am. Chem. Soc. 2003, 125, 5646-5647.
24. A. C. Frisch, N. Shaikh, A. Zapf, M. Beller, Angew. Chem. 2002, 114, 4218-4221; Angew. Chem. Int. Ed. 2002, 41, 4056-4059.
25. A. C. Frisch, N. Shaikh, A. Zapf, M. Beller, Angew. Chem. 2002, 114, 4218-4221; Angew. Chem. Int. Ed. 2002, 41, 4056-4059.
26. The following recent publications report iron-catalyzed arylations of alkyl halides using structurally undefined catalysts formed "in situ": a) M. Nakamura, K. Matsuo, S. Ito, E. Nakamura, J. Am. Chem. Soc. 2004, 126, 3686-3687;
27. b) T. Nagano, T. Hayashi, Org. Lett. 2004, 6, 1297-1299.
28. J. K. Kochi, Acc. Chem. Res. 1974, 7, 351-360.
29. a) A. Fürstner, A. Leitner, M. Méndez, H. Krause, J. Am. Chem. Soc. 2002, 124, 13 856-13 863;
30. b) A. Fürstner, A. Leitner, Angew. Chem. 2002, 114, 632-635; Angew. Chem. Int. Ed. 2002, 41, 609-612;
31. b) A. Fürstner, A. Leitner, Angew. Chem. 2002, 114, 632-635; Angew. Chem. Int. Ed. 2002, 41, 609-612;
32. c) A. Fürstner, A. Leitner, G. Seidel, Org. Synth., in press.
33. a) A. Fürstner, A. Leitner, Angew. Chem. 2003, 115, 320-323; Angew. Chem. Int. Ed. 2003, 42, 308-311;
34. a) A. Fürstner, A. Leitner, Angew. Chem. 2003, 115, 320-323; Angew. Chem. Int. Ed. 2003, 42, 308-311;
35. b) G. Seidel, D. Laurich, A. Fürstner, J. Org. Chem. 2004, 69, 3950-3952.
36. B. Scheiper, M. Bonnekessel, H. Krause, A. Fürstner, J. Org. Chem. 2004, 69, 3943-3949.
37. A. Fürstner, D. De Souza, L. Parra-Rapado, J. T. Jensen, Angew. Chem. 2003, 115, 5516-5518; Angew. Chem. Int. Ed. 2003, 42, 5358-5360.
38. A. Fürstner, D. De Souza, L. Parra-Rapado, J. T. Jensen, Angew. Chem. 2003, 115, 5516-5518; Angew. Chem. Int. Ed. 2003, 42, 5358-5360.
39. B. Scheiper, F. Glorius, A. Leitner, A. Fürstner, Proc. Natl. Natl. Acad. Sci. USA, in press.
40. A. Fürstner, M. Méndez, Angew. Chem. 2003, 115, 5513-5515; Angew. Chem. Int. Ed. 2003, 42, 5355-5357.
41. A. Fürstner, M. Méndez, Angew. Chem. 2003, 115, 5513-5515; Angew. Chem. Int. Ed. 2003, 42, 5355-5357.
42. A. Fürstner, H. Brunner, Tetrahedron Lett. 1996, 37, 7009-7012.
43. See the following for leading references on iron-catalyzed cross-coupling reactions from other laboratories: a) G. Cahiez, H. Avedissian, Synthesis 1998, 1199-1205;
44. b) H. Shinokubo, K. Oshima, Eur. J. Org. Chem. 2004, 2081-2091;
45. c) M. A. Fakhfakh, X. Franck, R. HocquemilIer, B. Figadère, J. Organomet. Chem. 2001, 624, 131-135;
46. d) M. Hocek, H. Dvoráková, J. Org. Chem. 2003, 68, 5773-5776;
47. ) B. Hölzer, R. W. Hoffmann, Chem. Commun. 2003, 732-733;
48. f) W. Dohle, F. Kopp, G. Cahiez, P. Knochel, Synlett 2001, 1901-1904;
49. g) M. Hojo, Y. Murakami, H. Aihara, R. Sakuragi, Y. Baba, A. Hosomi, Angew. Chem. 2001, 113, 641-643; Angew. Chem. Int. Ed. 2001, 40, 621-623;
50. g) M. Hojo, Y. Murakami, H. Aihara, R. Sakuragi, Y. Baba, A. Hosomi, Angew. Chem. 2001, 113, 641-643; Angew. Chem. Int. Ed. 2001, 40, 621-623;
51. h) M. Nakamura, A. Hirai, E. Nakamura, J. Am. Chem. Soc. 2000, 122, 978-979;
52. i) E. Alvarez, T. Cuvigny, C. Hervé du Penhoat, M. Julia, Tetrahedron 1988, 44, 119-126;
53. j) V. Fiandanese, G. Marchese, V. Martina, L. Ronzini, Tetrahedron Lett. 1984, 25, 4805-4808, and references therein.
54. B. Bogdanović, M. Schwickardi, Angew. Chem. 2000, 112, 4788-4790; Angew. Chem. Int. Ed. 2000, 39, 4610-4612.
55. B. Bogdanović, M. Schwickardi, Angew. Chem. 2000, 112, 4788-4790; Angew. Chem. Int. Ed. 2000, 39, 4610-4612.
56. a) K. Jonas, L. Schieferstein, C. Krüger, Y.-H. Tsay, Angew. Chem. 1979, 91, 590-591; Angew. Chem. Int. Ed. Engl. 1979, 18, 550-551;
57. a) K. Jonas, L. Schieferstein, C. Krüger, Y.-H. Tsay, Angew. Chem. 1979, 91, 590-591; Angew. Chem. Int. Ed. Engl. 1979, 18, 550-551;
58. b) see also: K. Jonas, L. Schieferstein, Angew. Chem. 1979, 91, 590; Angew. Chem. Int. Ed. Engl. 1979, 18, 549-550.
59. b) see also: K. Jonas, L. Schieferstein, Angew. Chem. 1979, 91, 590; Angew. Chem. Int. Ed. Engl. 1979, 18, 549-550.
60. B. H. Lipshutz, S. Sengupta, Org. React. 1992, 41, 135-631.
61. For a recent Pd-based method for the arylation of α-bromoacetate see: L. J. Gooßen, Chem. Commun. 2001, 669-670.
62. a) A. Yanagisawa, N. Nomura, H. Yamamoto, Tetrahedron 1994, 50, 6017-6028;
63. b) A. Yanagisawa, N. Nomura, H. Yamamoto, Synlett 1991, 513-514.
64. a) Y. Hayashi, H. Shinokubo, K. Oshima, Tetrahedron Lett. 1998, 39, 63-66;
65. b) see also: K. Wakabayashi, H. Yorimitsu, K. Oshima, J. Am. Chem. Soc. 2001, 123, 5374-5375.