Simplifying iron-phosphine catalysts for cross-coupling reactions

Angewandte Chemie - International Edition

Volumn 52, Issue 4, 2013, Pages 1285-1288

  Bedford, Robin B ^a   Carter, Emma ^b   Cogswell, Paul M ^a   Gower, Nicholas J ^a   Haddow, Mairi F ^a   Harvey, Jeremy N ^a   Murphy, Damien M ^b   Neeve, Emily C ^a   Nunn, Joshua ^a  

^a UNIVERSITY OF BRISTOL   (United Kingdom)

^b CARDIFF UNIVERSITY   (United Kingdom)

Author keywords

alkyl halides; catalysis; cross coupling; iron; phosphine ligands

Indexed keywords

ALKYL HALIDES; BIS-CHELATE COMPLEXES; CROSS COUPLING REACTIONS; CROSS-COUPLINGS; DIPHOSPHINE LIGAND; IRON CATALYST; PHOSPHINE LIGANDS; POOR PERFORMANCE;

CATALYSIS; CATALYSTS; ETHANE; LIGANDS; PHOSPHORUS COMPOUNDS;

IRON;

COORDINATION COMPOUND; IRON; LIGAND; PHOSPHINE; PHOSPHINE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMISTRY; CONFORMATION; X RAY CRYSTALLOGRAPHY;

CATALYSIS; COORDINATION COMPLEXES; CRYSTALLOGRAPHY, X-RAY; IRON; LIGANDS; MOLECULAR CONFORMATION; PHOSPHINES;

EID: 84872372519     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201207868     Document Type: Article

References (25)

1. R. B. Bedford, M. Betham, D. W. Bruce, A. A. Danopoulos, R. M. Frost, M. Hird, J. Org. Chem. 2006, 71, 1104
2. X. Lin, F. Zheng, F.-L. Qing, Organometallics 2012, 31, 1578.
3. R. B. Bedford, M. Huwe, M. C. Wilkinson, Chem. Commun. 2009, 600
4. T. Hatakeyama, Y. Kondo, Y. Fujiwara, H. Takaya, S. Ito, E. Nakamura, M. Nakamura, Chem. Commun. 2009, 1216.
5. R. B. Bedford, M. A. Hall, G. R. Hodges, M. Huwe, M. C. Wilkinson, Chem. Commun. 2009, 6430
6. T. Hatakeyama, T. Hashimoto, Y. Kondo, Y. Fujiwara, H. Seike, H. Takaya, Y. Tamada, T. Ono, M. Nakamura, J. Am. Chem. Soc. 2010, 132, 10674
7. T. Hashimoto, T. Hatakeyama, M. Nakamura, J. Org. Chem. 2012, 77, 1168
8. T. Hatakeyama, T. Hashimoto, K. K. A. D. S. Kathriarachchi, T. Zenmyo, H. Seike, M. Nakamura, Angew. Chem. 2012, 124, 8964
9. Angew. Chem. Int. Ed. 2012, 51, 8834.
10. S. Kawamura, K. Ishizuka, H. Takaya, M. Nakamura, Chem. Commun. 2010, 46, 6054
11. S. Kawamura, T. Kawabata, K. Ishizuka, M. Nakamura, Chem. Commun. 2012, 48, 9376.
12. For the alkynylation of alkyl halides, see:, T. Hatakeyama, Y. Okada, Y. Yoshimoto, M. Nakamura, Angew. Chem. 2011, 123, 11165
13. Angew. Chem. Int. Ed. 2011, 50, 10973.
14. For use with aryl Grignard reagents, see:, T. Hatakeyama, Y.-i. Fujiwara, Y. Okada, T. Itoh, T. Hashimoto, S. Kawamura, K. Ogata, H. Takaya, M. Nakamura, Chem. Lett. 2011, 40, 1030.
15. M. Tamura, J. K. Kochi, J. Am. Chem. Soc. 1971, 93, 1487
16. M. Tamura, J. Kochi, J. Organomet. Chem. 1971, 31, 289
17. M. Tamura, J. K. Kochi, Bull. Chem. Soc. Jpn. 1971, 44, 3063.
18. J. Kleimark, A. Hedström, P.-F. Larsson, C. Johansson, P.-O. Norrby, ChemCatChem 2009, 1, 152.
19. C. J. Adams, R. B. Bedford, E. Carter, N. J. Gower, M. F. Haddow, J. N. Harvey, M. Huwe, M. A. Cartes, S. M. Mansell, C. Mendoza, D. M. Murphy, E. C. Neeve, J. Nunn, J. Am. Chem. Soc. 2012, 134, 10333.
20. For a discussion, see:, J. E. Barclay, G. J. Leigh, A. Houlton, J. Silver, J. Chem. Soc. Dalton Trans. 1988, 2865.
21. 4, see:, A. Ekomié, G. Lefèvre, L. Fensterbank, E. Lacôte, M. Malacria, C. Ollivier, A. Jutand, Angew. Chem. 2012, 124, 7048
22. Angew. Chem. Int. Ed. 2012, 51, 6942.
23. D. L. DuBois, A. Miedaner, Inorg. Chem. 1986, 25, 4642.
24. To the best of our knowledge, the iron catalyzed cross-coupling of organoindium reagents has not been previously reported, although the iron-catalyzed annulation of arylindium reagents and alkynes was recently described, see:, L. Adak, N. Yoshikai, Tetrahedron 2012, 68, 5167.
25. M. Gargano, P. Giannocarro, M. Rossi, A. Sacco, J. Chem. Soc. Chem. Commun. 1973, 233b.