TMEDA in iron-catalyzed Kumada coupling: Amine adduct versus homoleptic "ate" complex formation

Angewandte Chemie - International Edition

Volumn 53, Issue 7, 2014, Pages 1804-1808

  Bedford, Robin B ^a   Brenner, Peter B ^a   Carter, Emma ^b   Cogswell, Paul M ^a   Haddow, Mairi F ^a   Harvey, Jeremy N ^a   Murphy, Damien M ^b   Nunn, Joshua ^a   Woodall, Christopher H ^a  

^a UNIVERSITY OF BRISTOL   (United Kingdom)

^b CARDIFF UNIVERSITY   (United Kingdom)

Author keywords

catalysis; cross coupling; Grignard reagents; iron

Indexed keywords

CHELATING DIAMINES; COMPLEX FORMATIONS; CROSS COUPLING REACTIONS; CROSS-COUPLINGS; GRIGNARD REAGENT; IRON CHLORIDES; TETRAMETHYLETHYLENEDIAMINE; X-RAY STRUCTURE;

AMINES; CATALYSIS; CHLORINE COMPOUNDS; IRON;

IRON COMPOUNDS;

EID: 84893625618     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201308395     Document Type: Article

References (31)

1. C. Bolm, J. Legros, J. Le Paih, L. Zani, Chem. Rev. 2004, 104, 6217
2. A. Fürstner, R. Martin, Chem. Lett. 2004, 33, 624
3. B. D. Sherry, A. Fürstner, Acc. Chem. Res. 2008, 41, 1500
4. W. M. Czaplik, M. Mayer, J. Cvengroš, A. J. von Wangelin, ChemSusChem 2009, 2, 396.
5. For stoichiometric addition of TMEDA, see:, M. Nakamura, K. Matsuo, S. Ito, E. Nakamura, J. Am. Chem. Soc. 2004, 126, 3686.
6. R. B. Bedford, D. W. Bruce, R. M. Frost, M. Hird, Chem. Commun. 2005, 4161
7. G. Cahiez, V. Habiak, C. Duplais, A. Moyeux, Angew. Chem. 2007, 119, 4442
8. Angew. Chem. Int. Ed. 2007, 46, 4364.
9. D. Noda, Y. Sunada, T. Hatakeyama, M. Nakamura, H. Nagashima, J. Am. Chem. Soc. 2009, 131, 6078.
10. V. W. Seidel, K.-J. Lattermann, Z. Anorg. Allg. Chem. 1982, 488, 69
11. M. Irwin, R. K. Jenkins, M. S. Denning, T. Krämer, F. Grandjean, G. J. Long, R. Herchel, J. E. McGrady, J. M. Goicoechea, Inorg. Chem. 2010, 49, 6160.
12. II ate complexes in C=C bond formation, see:, T. Kauffmann, Angew. Chem. 1996, 108, 401
13. Angew. Chem. Int. Ed. Engl. 1996, 35, 386.
14. TMEDA will also coordinate to ArMgX, increasing its nucleophilicity and thus the rates of transmetalation; for a discussion, see:, O. Vechorkin, V. Proust, X. Hu, J. Am. Chem. Soc. 2009, 131, 9756.
15. R. B. Bedford, M. Betham, D. W. Bruce, S. A. Davis, R. M. Frost, M. Hird, Chem. Commun. 2006, 1398.
16. D. H. Hill, A. Sen, J. Am. Chem. Soc. 1988, 110, 1650
17. D. H. Hill, M. A. Panez, A. Sen, J. Am. Chem. Soc. 1994, 116, 2889.
18. S. C. Bart, E. J. Hawrelak, A. K. Schmisseur, E. Lobkovsky, P. J. Chirik, Organometallics 2004, 23, 237.
19. H. Müller, W. Seidel, H. Görls, Angew. Chem. 1995, 107, 386
20. Angew. Chem. Int. Ed. Engl. 1995, 34, 325.
21. A. M. LaPointe, Inorg. Chim. Acta 2003, 345, 359.
22. A. Fürstner, R. Martin, H. Krause, G. Seidel, R. Goddard, C. W. Lehmann, J. Am. Chem. Soc. 2008, 130, 8773.
23. T. A. Bazhenova, R. M. Lobovskaya, R. P. Shibaeva, A. K. Shilova, M. Gruselle, G. Leny, E. Deschamps, J. Organomet. Chem. 1983, 244, 375.
24. P. J. Alonso, A. B. Arauzo, J. Forniés, M. Angeles García-Monforte, A. Martín, J. I. Martínez, B. Menjõn, C. Rillo, J. J. Sáiz-Garitaonandia, Angew. Chem. 2006, 118, 6859
25. Angew. Chem. Int. Ed. 2006, 45, 6707.
26. 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.
27. II dihydride. For the incorrect structure determination, see:, T. A. Bazhenova, R. M. Lobkovskaya, R. P. Shibaeva, A. E. Shilov, A. K. Shilova, M. Gruselle, G. Leny, B. Tchoubar, J. Organomet. Chem. 1983, 244, 265. For the corrected structure, see
28. J. M. Jefferis, G. S. Girolami, Organometallics 1998, 17, 3630.
29. A. Hedström, E. Lindstedt, P.-O. Norrby, J. Organometal. Chem. 2013, 748, 51
30. A. Hedström, U. Bollmann, J. Bravidor, P.-O. Norrby, Chem. Eur. J. 2011, 17, 11991
31. J. Kleimark, A. Hedström, P.-F. Larsson, C. Johansson, P.-O. Norrby, ChemCatChem 2009, 1, 152.