A catalytic application of Co/Zr heterobimetallic complexes: Kumada coupling of unactivated alkyl halides with alkyl grignard reagents

European Journal of Inorganic Chemistry

Volumn , Issue 13, 2011, Pages 2029-2033

  Zhou, Wen ^a   Napoline, Jonathan Wesley ^a   Thomas, Christine M ^a  

^a BRANDEIS UNIVERSITY   (United States)

Author keywords

Cobalt; Cross coupling; Heterometallic complexes; Metal metal interactions; Radical reactions

Indexed keywords

COBALT COMPOUNDS; FREE RADICAL REACTIONS; METAL HALIDES; REACTION KINETICS; ZIRCONIUM COMPOUNDS;

ALKYLHALIDES; CATALYTIC APPLICATIONS; CO COMPLEXES; CROSS-COUPLINGS; GRIGNARD REAGENT; HETERO BIMETALLIC COMPLEXES; HETEROBIMETALLICS; HETEROMETALLIC COMPLEXES; METAL-METAL INTERACTIONS; RADICAL REACTIONS;

CHLORINE COMPOUNDS;

EID: 79955055584     PISSN: 14341948     EISSN: 10990682     Source Type: Journal    
DOI: 10.1002/ejic.201100109     Document Type: Article

References (25)

1. J. F. Hartwig, Organotransition Metal Chemistry: From Bonding to Catalysis, University Science Books, Sausalito, CA, 2010.
2. J.-P. Corbet, G. Mignani, Chem. Rev. 2006, 106, 2651-2710.
3. S. Kotha, K. Lahiri, D. Kashinath, Tetrahedron 2002, 58, 9633-9695.
4. J. G. de Vries, Can. J. Chem. 2001, 79, 1086-1092.
5. K. C. Nicolaou, P. G. Bulger, D. Sarlah, Angew. Chem. Int. Ed. 2005, 44, 4442-4489.
6. T.-Y. Luh, M.-k. Leung, K.-T. Wong, Chem. Rev. 2000, 100, 3187-3204.
7. A. Rudolph, M. Lautens, Angew. Chem. Int. Ed. 2009, 48, 2656-2570.
8. Z. Csok, O. Vechorkin, S. B. Harkins, R. Scopelliti, X. Hu, J. Am. Chem. Soc. 2008, 130, 8156-8157.
9. O. Vechorkin, Z. Csok, R. Scopelliti, X. Hu, Chem. Eur. J. 2009, 15, 3889-3899.
10. O. Vechorkin, X. Hu, Angew. Chem. Int. Ed. 2009, 48, 2937-2940.
11. O. Vechorkin, V. Proust, X. Hu, J. Am. Chem. Soc. 2009, 131, 9756-9766.
12. K. G. Dongol, H. Koh, M. Sau, C. L. L. Chai, Adv. Synth. Catal. 2007, 349, 1015-1018.
13. T. Tsuji, H. Yorimitsu, K. Oshima, Angew. Chem. Int. Ed. 2002, 41, 4137-4139.
14. G. Cahiez, C. Chaboche, C. Duplais, A. Moyeux, Org. Lett. 2008, 10, 277-280.
15. H. Ohmiya, T. Tsuji, H. Yorimitsu, K. Oshima, Chem. Eur. J. 2004, 10, 5640-5648.
16. H. Ohmiya, K. Wakabayashi, H. Yorimitsu, K. Oshima, Tetrahedron 2006, 62, 2207-2213.
17. G. Cahiez, C. Chaboche, C. Duplais, A. Giulliani, A. Moyeux, Adv. Synth. Catal. 2008, 350, 1484-1488.
18. B. P. Greenwood, S. I. Forman, G. T. Rowe, C.-H. Chen, B. M. Foxman, C. M. Thomas, Inorg. Chem. 2009, 48, 6251-6260.
19. B. P. Greenwood, G. T. Rowe, C.-H. Chen, B. M. Foxman, C. M. Thomas, J. Am. Chem. Soc. 2010, 132, 44-45.
20. C. M. Thomas, J. W. Napoline, G. T. Rowe, B. M. Foxman, Chem. Commun. 2010, 46, 5790-5792.
21. G. Cahiez, V. Habiak, C. Duplais, A. Moyeux, Angew. Chem. Int. Ed. 2007, 46, 4364-4366.
22. M. Nakamura, K. Matsuo, S. Ito, E. Nakamura, J. Am. Chem. Soc. 2004, 126, 3686-3687.
23. L. Ford, U. Jahn, Angew. Chem. Int. Ed. 2009, 48, 6386-6389.
24. Based on the differences in the structure and reactivity of the chemical reduction product of 1 in comparison to 2 and 3, we anticipate that the cross-coupling reaction using catalyst 1 proceeds via a different mechanism.
25. TEMPO does not react with reduced complex 5 in the absence of alkyl halide substrates.