Iron nanoparticles in the coupling of alkyl halides with aryl Grignard reagents

Chemical Communications

Volumn , Issue 13, 2006, Pages 1398-1400

  Bedford, Robin B ^a   Betham, Michael ^a   Bruce, Duncan W ^b   Davis, Sean A ^a   Frost, Robert M ^c   Hird, Michael ^d  

^a UNIVERSITY OF BRISTOL   (United Kingdom)

^b UNIVERSITY OF YORK   (United Kingdom)

^c UNIVERSITY OF EXETER   (United Kingdom)

^d UNIVERSITY OF HULL   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYL GROUP; HALIDE; HEXANE; HYDROGEN; IRON; MACROGOL; REAGENT;

ARTICLE; CATALYST; CROSS COUPLING REACTION; CYCLIZATION; GRIGNARD REACTION; NANOPARTICLE; STOICHIOMETRY; TEMPERATURE DEPENDENCE;

EID: 33645025382     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/b601014h     Document Type: Article

References (28)

1. A. C. Frisch M. Beller Angew. Chem., Int. Ed. 2005 44 674
2. M. R. Netherton G. C. Fu Adv. Synth. Catal. 2004 346 1525
3. D. J. Cárdenas Angew. Chem., Int. Ed. 2003 42 384
4. T.-Y. Luh M.-K. Leung K.-T. Wong Chem. Rev. 2000 100 3187
5. J. K. Kochi J. Organomet. Chem. 2002 653 11
6. T. Nagano T. Hayashi Org. Lett. 2004 6 1297
7. R. Martin A. Fürstner Angew. Chem., Int. Ed. 2004 43 3955
8. A. Fürstner H. Krause C. W. Lehmann Angew. Chem., Int. Ed. 2006 45 440
9. R. B. Bedford D. W. Bruce R. M. Frost J. W. Goodby M. Hird Chem. Commun. 2004 2822
10. M. Nakamura K. Matsuo S. Ito E. Nakamura J. Am. Chem. Soc. 2004 126 3686
11. R. B. Bedford D. W. Bruce R. M. Frost M. Hird Chem. Commun. 2005 4161
12. R. B. Bedford M. Betham D. W. Bruce A. A. Danopoulos R. M. Frost M. Hird J. Org. Chem. 2006 71 1104
13. G. J. P. Britovsek M. Bruce V. C. Gibson B. S. Kimberley P. J. Maddox S. Mastroianni S. J. McTavish C. Redshaw G. A. Solan S. Strömberg A. J. P. White D. J. Williams J. Am. Chem. Soc. 1999 121 8728
14. R. K. O'Reilly V. C. Gibson A. J. P. White D. J. Williams J. Am. Chem. Soc. 2003 125 8450
15. Y. Koltypin N. Perkas A. Gedanken J. Mater. Chem. 2004 14 2975
16. L. Guo Q. Huang X.-Y. Li S. Yang Phys. Chem. Chem. Phys. 2001 3 1661
17. 4Cy, see ref. 8
18. EDX analysis reveals the presence of Mg, Cl and Br
19. No special precautions were taken to prevent oxidation of the iron nanoparticles in the TEM analyses, so it is likely that the majority of the iron is in the form of an amorphous oxide phase in all cases
20. 2MgBr reacts with a primary alkyl halide, see ref. 3
21. As in ref. 10b, powder XRD of a dried sample of 3 is inconclusive, probably because the particles are small and amorphous
22. TEM analysis of a sample of 4 shows much larger aggregates of more polydisperse particles - see supporting information
23. This decrease may correspond to some catalyst precipitation
24. A. H. M. de Vries J. M. C. A. Mulders J. H. M. Mommers H. J. W. Henderickx J. G. de Vries Org. Lett. 2003 5 3285
25. 3-PEG may play a role in nanoparticle stabilization with respect to aggregation beyond that played by the PEG, which may explain the low catalytic activity of 4
26. Y. Ikeda T. Nakamura H. Yorimitsu K. Oshima J. Am. Chem. Soc. 2002 124 6514
27. J. Terao H. Watanabe A. Ikumi H. Kuniyasu N. Kambe J. Am. Chem. Soc. 2002 124 4222
28. To the best of our knowledge, catalytic organic applications of iron nanoparticles are limited to Fischer-Tropsch synthesis, simulation of coal liquefaction, the hydrogenation of naphthalene, the hydroformylation of an alkene, denitrogenation of nitrogen compounds and the degradation of trichloroethylene. For leading references see: Small, 2005, 1, 482