Manganese- or iron-catalyzed homocoupling of grignard reagents using atmospheric oxygen as an oxidant

Journal of the American Chemical Society

Volumn 129, Issue 45, 2007, Pages 13788-13789

  Cahiez, Gérard ^a   Moyeux, Alban ^a   Buendia, Julien ^a   Duplais, Christophe ^a  

^a Allée du Réseau Jean Marie Buckmaster   (France)

Author keywords

[No Author keywords available]

Indexed keywords

IRON; MANGANESE; OXIDIZING AGENT; OXYGEN; REAGENT;

ARTICLE; CATALYSIS; CROSS COUPLING REACTION; OXIDATION; REACTION ANALYSIS;

CATALYSIS; COMBINATORIAL CHEMISTRY TECHNIQUES; INDICATORS AND REAGENTS; IRON; MANGANESE; MOLECULAR STRUCTURE; ORGANIC CHEMICALS; ORGANOMETALLIC COMPOUNDS; OXIDANTS; OXYGEN;

EID: 36148956710     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja075417k     Document Type: Article

References (20)

1. Nielsen, M. B.; Diederich. F. Chem. Rev. 2005, 105, 1837.
2. Cahiez, G.; Chaboche, C.; Mahuteau-Betzer, F.; Ahr, M. Org. Lett. 2005, 7, 1943.
3. Nagano, T.; Hayashi, T. Org. Lett. 2005, 7, 491.
4. For leading references about Fe-catalyzed cross-coupling reactions, see: (a) Cahiez, G.; Avedissian, H. Synthesis 1998, 1199.
5. (b) Fürstner, A.; Leitner, A.; Méndez, M.; Krause, H. J. Am. Chem. Soc. 2002, 124, 13856.
6. (c) Duplais, C.; Bures, F.; Korn, T.; Sapountzis, I.; Cahiez, G.; Knochel, P. Angew. Chem., Int. Ed. 2004, 43, 2968.
7. (d) Nakamura, M.; Matsuo, K.; Ito, S.; Nakamura, E. J. Am. Chem. Soc. 2004, 126, 3686.
8. (e) Nagano, T.; Hayashi, T. Org. Lett. 2004, 6, 1297.
9. (f) Bedford, R. B.; Bruce, D. W.; Frost, R.; M. Hird, M. Chem. Commun. 2005, 4161.
10. (g) Cahiez, G.; Habiak, V.; Duplais, C.; Moyeux, A. Angew. Chem., Int. Ed. 2007, 46, 4364.
11. (h) Cahiez, G.; Duplais, C.; Moyeux, A. Org. Lett. 2007, 9, 3253.
12. Krasovskiy, A.; Tishkov, A.; del Amo, V.; Mayr, H.; Knochel, P. Angew. Chem., Int. Ed. 2006, 45, 5010.
13. Walling, C.; Buckler, S. A. J. Am. Chem. Soc. 1955, 77, 6032. See also Supporting Information, S2.
14. See for instance: Mulzer, J.; Öhler, E. Topics in Organometallic Chemistry; Springer: Berlin, 2004; Vol. 13, pp 269-366.
15. Prepared from piperonal (see Supporting Information).
16. 2 only decomposes above 0°C: Maruyama, K.; Ito, T.; Yamamoto, A. Transition Met. Chem. 1980, 5, 14.
17. Lane, B. S.; Burgess, K. Chem. Rev. 2003, 103, 2457.
18. Adamo, C.; Amatore, C.; Ciofini, I.; Jutand, A.; Lakmini, H. J. Am. Chem. Soc. 2006, 128, 6829.
19. (a) Beermann, C.; Clauss, K. Angew. Chem. 1959, 71, 627.
20. (b) Cahiez, G. An. Quim. 1995, 91, 561. See also Supporting Information, S2.