Journal of the American Chemical Society
ARTICLE
a boiling solution of magnesium turnings (5.35 g, 0.22 mol) in 100 mL of
dry n-butyl ether under argon and refluxing the resulting gray solution
for 2 h. The solution was cooled to 263 K, and the system was evacuated
(17) Wei, C. S.; Jimenez-Hoyos, C. A.; Videa, M. F.; Hartwig, J. F.;
Hall, M. B. J. Am. Chem. Soc. 2010, 132, 3078.
(18) Bernskoetter, W. H.; Schauer, C. K.; Goldberg, K. I.; Brookhart,
M. Science 2009, 326, 553.
2 1
before the dropwise addition of 0.78 mL of D O. The propane-1-d
(
19) Lo, H. C.; Iron, M. A.; Martin, J. M. L.; Keinan, E. Chem.-Eur. J.
007, 13, 2812.
20) Bengali, A. A.; Hall, M. B.; Wu, H. Organometallics 2008, 27,
5826.
generated was passed through a trap at 227 K to remove n-butyl ether,
collected in a trap cooled at 157 K (ether liquid nitrogen slush bath), and
transferred into a glass bulb on a high vacuum line. The product was
2
(
65
characterized by IR and NMR spectroscopy. In the case of the
(21) Bengali, A. A.; Fan, W. Y. Organometallics 2008, 27, 5488.
experiments with CpRe(CO) , propane-1-d was purified following
3
1
13
(22) Weaver, J. F.; Hakanoglu, C.; Hawkins, J. M.; Asthagiri, A.
J. Chem. Phys. 2010, 132, 024709.
1
the same method as for propane-1- C purification. Butane-1-d (98
atom %D) was obtained from CDN isotopes and purified before use. In
this case, it was passed through a U-tube containing Pt/charcoal catalyst
at 243 K. Cyclopentane was purified before use by stirring with con-
(
(
(
23) Janak, K. E.; Parkin, G. J. Am. Chem. Soc. 2003, 125, 6889.
24) Jones, W. D. Inorg. Chem. 2005, 44, 4475.
25) Balcells, D.; Clot, E.; Eisenstein, O. Chem. Rev. 2010, 112,
centrated H
2 4 4
SO overnight, washing with water and drying over MgSO ,
749.
then storing over a potassium mirror.
(
(
26) Vastine, B. A.; Hall, M. B. Coord. Chem. Rev. 2009, 253, 1202.
27) Mkhalid, I. A. I.; Barnard, J. H.; Marder, T. B.; Murphy, J. M.;
’
ASSOCIATED CONTENT
Supporting Information. Spectra showing formation of
Hartwig, J. F. Chem. Rev. 2010, 110, 890.
28) Alcaraz, G.; Grellier, M.; Sabo-Etienne, S. Acc. Chem. Res. 2009,
42, 1640.
(
S
b
(
(
(
(
29) Corey, J. Y.; Braddock-Wilking, J. Chem. Rev. 1999, 99, 175.
CpRe(CO) (propane) and CpRe(CO) (butane). This material
2
2
30) Lin, Z. Y. Struct. Bonding (Berlin) 2008, 130, 123.
31) Nikonov, G. I. Adv. Organomet. Chem. 2005, 53, 217.
32) George, M. W.; Haward, M. T.; Hamley, P. A.; Hughes, C.;
is available free of charge via the Internet at http://pubs.acs.org.
’
AUTHOR INFORMATION
Johnson, F. P. A.; Popov, V. K.; Poliakoff, M. J. Am. Chem. Soc. 1993, 115,
286.
33) Cowan, A. J.; Portius, P.; Kawanami, H. K.; Jina, O. S.; Grills,
2
Corresponding Author
mike.george@nottingham.ac.uk; robin.perutz@york.ac.uk
(
D. C.; Sun, X.-Z.; McMaster, J.; George, M. W. Proc. Natl. Acad. Sci.
U.S.A. 2007, 104, 6933.
(
34) Alamiry, M. A. H.; Boyle, N. M.; Brookes, C. M.; George,
’
ACKNOWLEDGMENT
M. W.; Long, C.; Portius, P.; Pryce, M. T.; Ronayne, K. L.; Sun, X.-Z.;
Towrie, M.; Vuong, K. Q. Organometallics 2009, 28, 1461.
We thank the EPSRC (EP/D058031 and EP/D055768) and
the Universities of Nottingham and York for funding. O.T. would
like to thank the Ministerio de Ciencia e Innovaci ꢀo n and the
Fundaci ꢀo n Espa ~n ola para la Ciencia y la Tecnología for funding.
M.W.G. gratefully acknowledges receipt of a Royal Society
Wolfson Merit Award. We would also like to thank P. Fields,
R. Wilson, M. Guyler, C. Mortimer, and D. C. Williamson for
technical assistance. We thank Prof A. F. Lee for a sample of Pt on
charcoal.
(
35) Besora, M.; Carreon-Macedo, J. L.; Cowan, A. J.; George,
M. W.; Harvey, J. N.; Portius, P.; Ronayne, K. L.; Sun, X.-Z.; Towrie,
M. J. Am. Chem. Soc. 2009, 131, 3583.
(36) Calladine, J. A.; Vuong, K. Q.; Sun, X.-Z.; George, M. W. Pure
Appl. Chem. 2009, 81, 1667.
(
37) Sun, X.-Z.; Grills, D. C.; Nikiforov, S. M.; Poliakoff, M.; George,
M. W. J. Am. Chem. Soc. 1997, 119, 7521.
38) Childs, G. I.; Colley, C. S.; Dyer, J.; Grills, D. C.; Sun, X. Z.;
Yang, J. X.; George, M. W. J. Chem. Soc., Dalton Trans. 2000, 1901.
(
(
(
39) Cowan, A. J.; George, M. W. Coord. Chem. Rev. 2008, 252, 2504.
40) Childs, G. I.; Grills, D. C.; Sun, X.-Z.; George, M. W. Pure Appl.
’
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dx.doi.org/10.1021/ja110451k |J. Am. Chem. Soc. 2011, 133, 2303–2310