Iron-catalyzed homo-coupling of simple and functionalized arylmagnesium reagents

Organic Letters

Volumn 7, Issue 10, 2005, Pages 1943-1946

  Cahiez, Gérard ^a   Chaboche, Christophe ^a   Mahuteau Betzer, Florence ^a   Ahr, Mathieu ^a  

^a Allée du Réseau Jean Marie Buckmaster   (France)

Author keywords

[No Author keywords available]

Indexed keywords

IRON; MAGNESIUM; METHYL GROUP; N METHYLCRINASIADINE; NITROGEN DIOXIDE; REAGENT; UNCLASSIFIED DRUG;

ARTICLE; CYCLIZATION; SYNTHESIS;

CATALYSIS; CYCLIZATION; HETEROCYCLIC COMPOUNDS WITH 4 OR MORE RINGS; INDICATORS AND REAGENTS; IRON; LILIACEAE; MAGNESIUM; MOLECULAR STRUCTURE;

EID: 19544373479     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol050340v     Document Type: Article

References (29)

1. (a) Cahiez, G.; Marquais, S. Pure Appl. Chem. 1996, 68, 669.
2. (b) Cahiez, G.; Marquais, S. Tetrahedron Lett. 1996, 37, 1773.
3. (c) Cahiez, G.; Avedissian, H. Synthesis 1998, 1199.
4. (d) Dohle, W.; Koppe, F.; Cahiez, G.; Knochel, P. Synlett 2001, 12, 1901.
5. (a) Fürstner, A.; Leitner, A.; Méndez, M.; Krause, H. J. Am. Chem. Soc. 2002, 124, 13856.
6. (b) Fürstner, A.; Leitner, A. Angew. Chem., Int. Ed. 2002, 41, 609.
7. (c) Quintin, J.; Frank, X. Hocquemiller, R.; Figadère, B. Tetrahedron Lett. 2002, 43, 3547.
8. (d) Martin, R.; Fürstner, A. Angew. Chem., Int. Ed. 2004, 43, 3955.
9. (e) Scheiper, B. Bonnekessel, M.; Krause, H.; Fürstner, A. J. Org. Chem. 2004, 69, 3943.
10. (f) Nakamura, M.; Matsuo, K.; Ito, S.; Nakamura, E. J. Am. Chem. Soc. 2004, 126, 3686.
11. (g) Nagano, T.; Hayashi, T. Org. Lett. 2004, 6, 1297.
12. Metal-Catalysed Cross-Coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wiley-WCH: Weinheim, 1998.
13. For review on aryl-aryl coupling reactions, see: (a) Stanforth, S. Tetrahedron 1998, 54, 263.
14. (b) Hassan, J.; Sévignon, M.; Gozzi, C.; Schultz, E.; Lemaire, M. Chem. Rev. 2002, 102, 1359.
15. Nagano, T.; Hayashi, T. Org. Lett. 2005, 7, 491.
16. (a) Boymond, L.; Röttländer, M.; Cahiez, G.; Knochel, P. Angew. Chem. Int. Ed. 1998, 37, 1701.
17. (b) Rottländer, M.; Boymond, L.; Bérillon, L.; Leprêtre, A.; Varchi, G.; Avolio, S.; Laaziri, H.; Quéguiner, G.; Ricci, A.; Cahiez, G.; Knochel, P. Chem. Eur. J. 2000, 6, 767.
18. For a review, see: Knochel, P.; Dohle, W.; Gommermann, N.; Kneisel, F. F.; Kopp, F.; Korn, T.; Sapountzis, I.; Anh Vu, V. Angew. Chem., Int. Ed. 2003, 42, 4302.
19. Sapountzis, I.; Knöchel, P. Angew. Chem., Int. Ed. 2002, 4, 1610.
20. Until 40% yield of cross-coupling product between the starting aryl Grignard reagent and i-PrI were obtained. The iron-catalyzed cross-coupling reaction between arylmagnesium reagent and secondary alkyl halide in THF has been reported: (a) Nakamura, M.; Matsuo, K.; Ito, S.; Nakamura, E. J. Am. Chem. Soc. 2004, 126, 3686.
21. (b) Martin, R.; Fürstner, A. Angew. Chem., Int. Ed. 2004, 43, 3955.
22. The reaction can also be performed in ether: Nagano, T.; Hayashi, T. Org. Lett. 2004, 6, 1297.
23. Rocca, P.; Cochennec, C.; Marsais, F.; Thomas-dit-Dumont, L.; Mallet, M.; Godard, A.; Quéguiner, G. J. Org. Chem. 1993, 58, 7832.
24. Suau, R.; Gomez, A. I.; Rico, R. Phytochemistry 1990, 29, 1710.
25. 6-Bromopiperonal 7 was prepared according to Conrad, P. C.; Kwiatkowski, P. L.; Fuchs, P. L. J. Org. Chem. 1987, 52, 586.
26. 6-Iodopiperonal 8 was prepared from 7 according to Bogucki, D. E.; Charlton, J. L. J. Org. Chem. 1995, 60, 588.
27. For the oxidation of 8 to the corresponding carboxylic acid (8 to 9, step 1), see: Padwa, A.; Brodney, M. A.; Lynch, S. M. J. Org. Chem. 2001, 66, 1716.
28. (a) Neumann, S. M.; Kochi, J. K. J. Org. Chem. 1975, 40, 599.
29. (b) Smith, R. S.; Kochi, J. K. J. Org. Chem. 1976, 41, 502.