Iron-catalyzed homocoupling of bromide compounds

Journal of Organic Chemistry

Volumn 71, Issue 17, 2006, Pages 6637-6639

  Xu, Xiaoliang ^a   Cheng, Dongping ^a   Pei, Wen ^a  

^a ZHEJIANG UNIVERSITY OF TECHNOLOGY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

HOMOCOUPLING REACTIONS; IRON SALTS; IRON-CATALYZED HOMOCOUPLING; OXIDANTS;

CATALYSIS; CATALYSTS; IRON; MAGNESIUM PRINTING PLATES; REACTION KINETICS;

BROMINE COMPOUNDS;

AROMATIC COMPOUND; BROMIDE; HALOGEN; IRON SALT; MAGNESIUM; OXIDIZING AGENT;

ADDITION REACTION; ARTICLE; CATALYSIS; COMPLEX FORMATION; GRIGNARD REACTION; QUANTUM YIELD; REACTION ANALYSIS; STOICHIOMETRY;

BROMIDES; CATALYSIS; IRON; MOLECULAR STRUCTURE; TITANIUM; TOLUENE; VANADIUM;

EID: 33747419242     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo060673l     Document Type: Article

References (58)

1. For cross-coupling, see (a) Cross-Coupling Reactions. A Practical Guide; Miyaura, N., Ed.; Topics in Current Chemistry; Springer: Berlin, 2002; Vol. 219.
2. (b) Palladium in Heterocyclic Chemistry: A Guide for the Synthetic Chemist; Li, J. J., Gribble, G. W., Eds.; Elsevier: Oxford, U.K., 2000.
3. (c) Suzuki, A. J. Organomet. Chem. 1999, 576, 147.
4. (d) Duncton, M. A. J.; Pattenden, G. J. Chem. Soc., Perkin Trans, 1 1999, 1235.
5. (e) Metal-catalyzed Cross-coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wiley-VCH: Weinheim, Germany, 1998.
6. (f) Farina, V.; Krishnamurthy, V.; Scott, W. J. Org. React. 1997, 50, 1.
7. (g) Rossi, R.; Carpita, A.; Bellina, F. Org. Prep. Proced. Int. 1995, 27, 127.
8. (h) Snieckus, V. Pure Appl. Chem. 1994, 66, 2155.
9. (i) Knight, D. W. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, U.K., 1991; Vol. 3, p 481.
10. (j) Stille, J. K. Angew. Chem., Int. Ed. Engl. 1986, 25, 508.
11. (k) Negishi, E. Acc. Chem. Res. 1982, 15, 340.
12. (l) Kumada, M. Pure Appl. Chem. 1980, 52, 669.
13. For self-coupling, see (a) Bringmann, G.; Walter, R.; Weirich, R. Angew. Chem., Int. Ed. Engl. 1990, 29, 977.
14. (b) Sainsbury, M. Tetrahedron 1980, 36, 3327.
15. (c) Fanta, P. E. Chem. Rev. 1946, 38, 139;
16. (c) Fanta, P. E. Chem. Rev. 1964, 64, 613;
17. Synthesis 1974, 9.
18. (d) Goshaev, M.; Otroshchenko, O. S.; Sadykov, A. S. Russ. Chem. Soc. Rev. 1972, 41, 1046.
19. (e) Posner, G. H. An Introduction to Synthesis Using Organocopper Reagents; John Wiley: New York, 1980.
20. (f) Nelson, T. P.; Meyers, A. I. J. Org. Chem. 1994, 59, 2655.
21. (a) Handbook of Combinatorial Chemistry: Drugs, Catalysts, Materials; Nicolaou, K. C., Hanko, R., Hartwig, W., Eds.; Wiley-VCH: Weinheim, Germany, 2002.
22. (b) Beller, M.; Zapf, A.; Mägerlein, W. Chem. Eng. Technol. 2001, 24, 575.
23. (a) Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E., Ed.; Wiley: New York, 2002.
24. (b) Tsuji, J. Palladium Reagents and Catalysts: Innovations in Organic Synthesis; Wiley: New York, 1996.
25. (c) Trost, B. M.; Verhoeven, T. R. In Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon: Oxford, U.K., 1982; Vol. 8, p 799.
26. (a) Kochi, J. K. J. Organomet. Chem. 2002, 653, 11.
27. (b) Smith, R. S.; Kochi, J. K. J. Org. Chem. 1976, 41, 502.
28. (c) Neumann, S. M.; Kochi, J. K. J. Org. Chem. 1975, 40, 599.
29. (d) Kochi, J. K. Acc. Chem. Res. 1974, 7, 351.
30. (f) Tamura, M.; Kochi, J. K. J. Am. Chem. Soc. 1971, 93, 1487.
31. (g) Tamura, M.; Kochi, J. K. Bull. Chem. Soc. Jpn. 1971, 44, 3063.
32. (h) Tamura, M.; Kochi, J. K. Synthesis 1971, 303.
33. Recent reviews: (a) Fürstner, A.; Martin, R. Chem. Lett. 2005, 34, 624.
34. (b) Shinokubo, H.; Oshima, K. Eur. J. Org. Chem. 2004, 2081.
35. (c) Bolm, C.; Legros, J.; Le Paih, J.; Zani, L. Chem. Rev. 2004, 104, 6217.
36. (a) Bica, K.; Gaertner, P. Org. Lett. 2006, 8, 733.
37. (b) Bedford, B. R.; Betham, M.; Bruce, W. D.; Danopoulos, A. A.; Frost, M. R.; Hird, M. J. Org. Chem. 2006, 71, 1104.
38. (c) Bedford, B. R.; Bruce, W. D.; Frost, M. R.; Hird, M. Chem. Commun. 2005, 4161.
39. (d) Bedford, B. R.; Bruce, W. D.; Frost, M. R.; Goodby, W. J.; Hird, M. Chem. Commun. 2004, 2822.
40. (e) Martin, R.; Fürstner, A. Angew. Chem., Int. Ed. 2004, 43, 3955.
41. (f) Nagano, T.; Hayashi, T. Org. Lett. 2004, 6, 1297.
42. (g) Fürstner, A.; Leitner, A. Angew. Chem., Int. Ed. 2003, 42, 308.
43. (h) Fürstner, A.; De Souza, D.; Parra-Rapado, L.; Jensen, J. T. Angew. Chem., Int. Ed. 2003, 42, 5358.
44. (i) Nakamura, M.; Matsuo, K.; Inoue, T.; Nakamura, E. Org. Lett. 2003, 5, 1373.
45. (j) Fürstner, A.; Leitner, A. Angew. Chem., Int. Ed. 2002, 41, 609.
46. (k) Fürstner, A.; Leitner, A.; Méndez, M.; Krause, H. J. Am. Chem. Soc. 2002, 124, 13856.
47. (l) Hojo, M.; Murakami, Y.; Aihara, H.; Sakuragi, R.; Baba, Y.; Hosomi, A. Angew. Chem., Int. Ed. 2001, 40, 621.
48. (m) Nakamura, M.; Hirai, A.; Nakamura, E. J. Am. Chem. Soc. 2000, 122, 978.
49. (n) Cahiez, G.; Avedissian, H.; Synthesis 1998, 1199.
50. (o) Yanagisawa, A.; Nomura, N.; Yamamoto, H. Tetrahedron 1994, 50, 6017.
51. (p) Yanagisawa, A.; Nomura, N.; Yamamoto, H. Synlett 1991, 513.
52. (a) Nagano, T.; Hayashi, T. Org. Lett. 2005, 7, 491.
53. (b) Cahiez, G.; Chaboche, C.; Mahuteau-Betzer, F.; Ahr, M. Org. Lett. 2005, 7, 1943.
54. Bönnemann, H.; Bogdanović, B.; Brinkmann, R.; Spliethoff, B.; He, D. W. J. Organomet. Chem. 1993, 451 (1-2), 23.
55. According to Prof. H. B. Kagan's report, anhydrous THF can act as a proton source. (a) Kagan, H. B.; Namy, J. L.; Girard, P. Tetrahedron 1981, 37(Suppl 1). 175.
56. (b) Kagan, H. B. New. J. Chem. 1990, 14, 453.
57. Bogdanovic, B.; Schwickardi, M. Angew. Chem., Int. 2000, 39, 4610.
58. 3-catalyzed coupling reaction of phenylbromide magnesium reagent with bromobenzene in a ratio of 1:1 was investigated. It gave the biphenyl in 73% yield.