Redox-active ligand-mediated oxidative addition and reductive elimination at square planar cobalt(III): Multielectron reactions for cross-coupling

Journal of the American Chemical Society

Volumn 132, Issue 41, 2010, Pages 14358-14360

  Smith, Aubrey L ^a   Hardcastle, Kenneth I ^b   Soper, Jake D ^a  

^a GEORGIA INSTITUTE OF TECHNOLOGY   (United States)

^b EMORY UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYL HALIDES; C-C COUPLING; COORDINATE COMPLEXES; CROSS-COUPLINGS; ELECTROPHILIC ADDITION REACTIONS; METAL FRAGMENTS; METAL OXIDATION; MULTI-ELECTRON; ORGANOMETALLIC COMPLEX; ORGANOZINC REAGENTS; OXIDATION STATE; OXIDATIVE ADDITIONS; REDOX-ACTIVE; REDOX-ACTIVE LIGAND; REDUCTANTS; REDUCTIVE ELIMINATION; REDUCTIVE ELIMINATION REACTION; STARTING MATERIALS;

ALKYLATION; COBALT; COBALT COMPOUNDS; LIGANDS; NUCLEOPHILES; ORGANOMETALLICS; OXIDATION; REDOX REACTIONS; SPHERES;

ADDITION REACTIONS;

AMIDOPHENOLATE LIGAND; COBALT COMPLEX; HALIDE; NUCLEOPHILE; ORGANOMETALLIC COMPOUND; PHENOL DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL BOND; CHEMICAL REACTION; COMPLEX FORMATION; CROSS COUPLING REACTION; CRYSTAL STRUCTURE; ELECTRON TRANSPORT; ELECTROSPRAY MASS SPECTROMETRY; OXIDATION REDUCTION REACTION;

EID: 77958056806     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja106212w     Document Type: Article

References (33)

1. For example, see: Metal-Catalyzed Cross-Coupling Reactions; Diederich, F. and Stang, P. J., Eds.; Wiley-VCH: Weinheim, Germany, 1998.
2. Chirik, P. J. and Wieghardt, K. Science 2010, 327, 794-795
3. For some recent examples, see
4. Czaplik, W. M., Mayer, M., Cvengros, J., and Jacobi von Wangelin, A. ChemSusChem 2009, 2, 396-417
5. Oshima, K. Bull. Chem. Soc. Jpn. 2008, 81, 1-24
6. Cahiez, G. and Moyeux, A. Chem. Rev. 2010, 110, 1435-1462
7. Sherry, B. D. and Fürstner, A. Acc. Chem. Res. 2008, 41, 1500-1511
8. Gosmini, C., Bégouin, J.-M., and Moncombie, A. Chem. Commun. 2008, 3221-3223
9. Frisch, A. C. and Beller, M. Angew. Chem., Int. Ed. 2005, 44, 674-688
10. Noda, D., Sunada, Y., Hatakeyama, T., Nakamura, M., and Nagashima, H. J. Am. Chem. Soc. 2009, 131, 6078-6079
11. Rudolph, A. and Lautens, M. Angew. Chem., Int. Ed. 2009, 48, 2656-2670
12. Liu, W., Cao, H., and Lei, A. Angew. Chem., Int. Ed. 2010, 49, 2004-2008
13. Cárdenas, D. J. and Phapale, V. B. Chem. Soc. Rev. 2009, 38, 1598-1607
14. Zhou, J. S. and Fu, G. C. J. Am. Chem. Soc. 2003, 125, 14726-14727
15. Vechorkin, O. and Hu, X. Angew. Chem., Int. Ed. 2009, 48, 1-5
16. For recent examples, see
17. Nguyen, A. I., Blackmore, K. J., Carter, S. M., Zarkesh, R. A., and Heyduk, A. F. J. Am. Chem. Soc. 2009, 131, 3307-3316
18. Ketterer, N. A., Fan, H., Blackmore, K. J., Yang, X., Ziller, J. W., Baik, M.-H., and Heyduk, A. F. J. Am. Chem. Soc. 2008, 130, 4364-4374
19. Haneline, M. R. and Heyduk, A. F. J. Am. Chem. Soc. 2006, 128, 8410-8411
20. Stanciu, C., Jones, M. E., Fanwick, P. E., and Abu-Omar, M. M. J. Am. Chem. Soc. 2007, 129, 12400-12401
21. Bowman, A. C., Milsmann, C., Atienza, C. C. H., Lobkovsky, E., Wieghardt, K., and Chirik, P. J. J. Am. Chem. Soc. 2010, 132, 1676-1684
22. Lu, C. C., Weyhermüller, T., Bill, E., and Wieghardt, K. Inorg. Chem. 2009, 48, 6055-6064
23. Lippert, C. A., Arnstein, S., Sherill, D., and Soper, J. D. J. Am. Chem. Soc. 2010, 132, 3879-3892
24. Smith, A. L., Clapp, L. A., Hardcastle, K. I., and Soper, J. D. Polyhedron 2010, 29, 164-169
25. Bill, E., Bothe, E., Chaudhuri, P., Chlopek, K., Herebian, D., Kokatam, S., Ray, K., Weyhermüller, T., Neese, F., and Wieghardt, K. Chem.-Eur. J. 2005, 11, 204-224
26. Poddel'sky, A. I., Cherkasov, V. K., and Abakumov, G. A. Coord. Chem. Rev. 2009, 253, 291-324
27. 12 models is typically weak and homolyzed in visible light. See: Schrauzer, G. N., Sibert, J. W., and Windgassen, R. J. J. Am. Chem. Soc. 1968, 90, 6681-6688
28. Crabtree, R. H. The Organometallic Chemistry of the Transition Metals, 3rd ed.; Wiley: New York, 2001.
29. 2X likely further highlights the sensitivity of the reaction to steric hindrance.
30. Ar) decomposition product.
31. 2-.
32. In both reactions the balance of the cobalt-derived ethyls was not found. These may form butane, which is not quantitated by the GC-MS method used.
33. For example, see: Labinger, J. A. and Osborn, J. A. Inorg. Chem. 1980, 19, 3230-3236 and references therein