Organometallics
Article
benzophenone, 7.94; diphenylmethanol, 12.57. All of the conversions
were reported as an average of two GC runs. The reported conversions
were reproducible.
6172−6173. (e) Ikariya, T.; Gridnev, I. D. Chem. Rec. 2009, 9, 106−
123.
(5) (a) Standfest-Hauser, C.; Slugovc, C.; Mereiter, K.; Schmid, R.;
Kirchner, K.; Xiao, L.; Weissensteiner, W. Dalton Trans. 2001, 2989−
2995. (b) Ito, M.; Hirakawa, M.; Murata, K.; Ikariya, T. Organo-
metallics 2001, 20, 379−381. (c) Leong, C. G.; Akotsi, O. M.;
Ferguson, M. J.; Bergens, S. H. Chem. Commun. 2003, 750−751.
(d) Lundgren, R. J.; Rankin, M. A.; McDonald, R.; Schatte, G.;
Stradiotto, M. Angew. Chem., Int. Ed. 2007, 46, 4732−4735. (e) Ma,
G. B.; McDonald, R.; Ferguson, M.; Cavell, R. G.; Patrick, B. O.;
James, B. R.; Hu, T. Q. Organometallics 2007, 26, 846−854. (f) Baratta,
W.; Ballico, M.; Esposito, G.; Rigo, P. Chem. Eur. J. 2008, 14, 5588−
5595. (g) Sandoval, C. A.; Shi, Q. X.; Liu, S. S.; Noyori, R. Chem.-Asian
J. 2009, 4, 1221−1224. (h) Phillips, S. D.; Fuentes, J. A.; Clarke, M. L.
Chem. Eur. J. 2010, 16, 8002−8005. (i) Soni, R.; Cheung, F. K.;
Clarkson, G. C.; Martins, J. E. D.; Graham, M. A.; Wills, M. Org.
Biomol. Chem. 2011, 9, 3290−3294.
(6) (a) O, W. W. N.; Lough, A. J.; Morris, R. H. Organometallics
2009, 28, 6755−6761. (b) O, W. W. N.; Lough, A. J.; Morris, R. H.
Chem. Commun. 2010, 46, 8240−8242. (c) O, W. W. N.; Lough, A. J.;
Morris, R. H. Organometallics 2011, 30, 1236−1252.
(7) O, W. W. N.; Lough, A. J.; Morris, R. H. Organometallics 2012,
DOI: 10.1021/om300108p.
(8) (a) Casey, C. P.; Johnson, J. B.; Singer, S. W.; Cui, Q. J. Am.
Chem. Soc. 2005, 127, 3100−3109. (b) Heiden, Z. M.; Rauchfuss, T. B.
J. Am. Chem. Soc. 2009, 131, 3593−3600. (c) Casey, C. P.; Johnson,
J. B.; Jiao, X. D.; Beetner, S. E.; Singer, S. W. Chem. Commun. 2010,
46, 7915−7917.
Computational Details. All density functional theory (DFT)
calculations were performed using the Gaussian 0339 and 0940 pack-
ages with the restricted hybrid mPW1PW91 functional.41 Iridium was
treated with the SDD42 relativistic effective core potential and an
associated basic set. All other atoms were treated with the double-ζ
basis set 6-31++G**, which includes diffuse functionals43 and addi-
tional p orbitals on hydrogen as well as additional d orbitals on carbon,
nitrogen, and oxygen.44 All geometry optimizations were conducted in
the gas phase, and the stationary points were characterized by normal-
mode analysis. Reported free energies were obtained at 1 atm and
298 K using unscaled vibrational frequencies. The QST3 method was
used to locate transition states. All transition states reported were
found to have a single imaginary frequency.
ASSOCIATED CONTENT
■
S
* Supporting Information
CIF files giving X-ray structural data for complexes 3, 4, 6, and
8, text, tables, and figures giving details for catalysis, Cartesian
coordinates, energies for all of the computed structures, and the
complete citation for refs 39 and 40, and AVI files giving
animations for loose vibrations characterizing the computed
transition states. This material is available free of charge via the
(9) (a) Dahlenburg, L.; Herbst, K.; Zahl, A. J. Organomet. Chem.
2000, 616, 19−28. (b) Dahlenburg, L.; Gotz, R. Eur. J. Inorg. Chem.
2004, 888−905. (c) Dahlenburg, L.; Gotz, R. Inorg. Chim. Acta 2004,
357, 2875−2880. (d) Li, Y.-Y.; Zhang, H.; Chen, J.-S.; Liao, X.-L.;
Dong, Z.-R.; Gao, J.-X. J. Mol. Catal. A 2004, 218, 153−156. (e) Chen,
J.-S.; Li, Y.-Y.; Dong, Z.-R.; Li, B.-Z.; Gao, J.-X. Tetrahedron Lett. 2004,
45, 8415−8418. (f) Dong, Z.-R.; Li, Y.-Y.; Chen, J.-S.; Li, B.-Z.; Xing,
Y.; Gao, J.-X. Org. Lett. 2005, 7, 1043−1045. (g) Clarke, Z. E.; Maragh,
P. T.; Dasgupta, T. P.; Gusev, D. G.; Lough, A. J.; Abdur-Rashid, K.
Organometallics 2006, 25, 4113−4117. (h) Choualeb, A.; Lough, A. J.;
Gusev, D. G. Organometallics 2007, 26, 5224−5229. (i) Chen, X. H.;
Jia, W. L.; Guo, R. W.; Graham, T. W.; Gullons, M. A.; Abdur-Rashid,
K. Dalton Trans. 2009, 1407−1410.
AUTHOR INFORMATION
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Corresponding Author
Notes
The authors declare no competing financial interest.
ACKNOWLEDGMENTS
■
The NSERC of Canada is thanked for a Discovery Grant to
R.H.M. and a graduate scholarship to W.W.N.O.
REFERENCES
(10) (a) Hillier, A. C.; Lee, H. M.; Stevens, E. D.; Nolan, S. P.
Organometallics 2001, 20, 4246−4252. (b) Albrecht, M.;
Miecznikowski, J. R.; Samuel, A.; Faller, J. W.; Crabtree, R. H.
■
(1) (a) Noyori, R.; Yamakawa, M.; Hashiguchi, S. J. Org. Chem. 2001,
66, 7931−7944. (b) Clapham, S. E.; Hadzovic, A.; Morris, R. H. Coord.
Chem. Rev. 2004, 248, 2201−2237. (c) Ito, M.; Ikariya, T. Chem.
Commun. 2007, 5134−5142. (d) Ikariya, T. Bull. Chem. Soc. Jpn. 2011,
84, 1−16.
Organometallics 2002, 21, 3596−3604. (c) Turkmen, H.; Pape, T.;
̈
Hahn, F. E.; Çetinkaya, B. Eur. J. Inorg. Chem. 2008, 2008, 5418−5423.
(d) da Costa, A. P.; Viciano, M.; Sanau, M.; Merino, S.; Tejeda, J.;
Peris, E.; Royo, B. Organometallics 2008, 27, 1305−1309. (e) Zinner,
S. C.; Rentzsch, C. F.; Herdtweck, E.; Herrmann, W. A.; Kuhn, F. E.
Dalton Trans. 2009, 7055−7062. (f) Gnanamgari, D.; Sauer, E. L. O.;
Schley, N. D.; Butler, C.; Incarvito, C. D.; Crabtree, R. H.
Organometallics 2009, 28, 321−325.
(2) (a) Abdur-Rashid, K.; Clapham, S. E.; Hadzovic, A.; Harvey,
J. N.; Lough, A. J.; Morris, R. H. J. Am. Chem. Soc. 2002, 124, 15104−
15118. (b) Rautenstrauch, V.; Hoang-Cong, X.; Churlaud, R.; Abdur-
Rashid, K.; Morris, R. H. Chem. Eur. J. 2003, 9, 4954−4967. (c) Abbel,
R.; Abdur-Rashid, K.; Faatz, M.; Hadzovic, A.; Lough, A. J.; Morris,
R. H. J. Am. Chem. Soc. 2005, 127, 1870−1882. (d) Zimmer-De Iuliis,
M.; Morris, R. H. J. Am. Chem. Soc. 2009, 131, 11263−11269.
(3) (a) Sandoval, C. A.; Ohkuma, T.; Muniz, K.; Noyori, R. J. Am.
Chem. Soc. 2003, 125, 13490−13503. (b) Hamilton, R. J.; Leong,
C. G.; Bigam, G.; Miskolzie, M.; Bergens, S. H. J. Am. Chem. Soc. 2005,
127, 4152−4153. (c) Hedberg, C.; Kallstrom, K.; Arvidsson, P. I.;
Brandt, P.; Andersson, P. G. J. Am. Chem. Soc. 2005, 127, 15083−
15090. (d) Di Tommaso, D.; French, S. A.; Catlow, C. R. A. J. Mol.
Struct. (THEOCHEM) 2007, 812, 39−49. (e) Puchta, R.; Dahlenburg,
L.; Clark, T. Chem. Eur. J. 2008, 14, 8898−8903. (f) Chen, Y.; Tang,
Y. H.; Lei, M. Dalton Trans. 2009, 2359−2364. (g) Lei, M.; Zhang,
W. C.; Chen, Y.; Tang, Y. H. Organometallics 2010, 29, 543−548.
(4) (a) Abdur-Rashid, K.; Faatz, M.; Lough, A. J.; Morris, R. H. J. Am.
Chem. Soc. 2001, 123, 7473−7474. (b) Clapham, S. E.; Morris, R. H.
Organometallics 2005, 24, 479−481. (c) Hadzovic, A.; Song, D.;
MacLaughlin, C. M.; Morris, R. H. Organometallics 2007, 26, 5987−
5999. (d) Ito, M.; Kitahara, S.; Ikariya, T. J. Am. Chem. Soc. 2005, 127,
(11) (a) Lee, H. M.; Lee, C. C.; Cheng, P. Y. Curr. Org. Chem. 2007,
11, 1491−1524. (b) Hahn, F. E.; Jahnke, M. C. Angew. Chem., Int. Edit.
2008, 47, 3122−3172. (c) Normand, A. T.; Cavell, K. J. Eur. J. Inorg.
Chem. 2008, 2781−2800. (d) Diez-Gonzalez, S.; Marion, N.; Nolan,
S. P. Chem. Rev. 2009, 109, 3612−3676. (e) Corberan, R.; Mas-Marza,
E.; Peris, E. Eur. J. Inorg. Chem. 2009, 1700−1716.
(12) (a) Crabtree, R. H.; Lavin, M.; Bonneviot, L. J. Am. Chem. Soc.
1986, 108, 4032−4037. (b) Arliguie, T.; Chaudret, B.; Morris, R. H.;
Sella, A. Inorg. Chem. 1988, 27, 598−599.
(13) Alcaraz, G.; Chaplin, A. B.; Stevens, C. J.; Clot, E.; Vendier, L.;
Weller, A. S.; Sabo-Etienne, S. Organometallics 2010, 29, 5591−5595.
(14) Handgraaf, J. W.; Reek, J. N. H.; Meijer, E. J. Organometallics
2003, 22, 3150−3157.
(15) (a) Hanasaka, F.; Fujita, K.; Yamaguchi, R. Organometallics
2005, 24, 3422−3433. (b) Hanasaka, F.; Fujita, K.-i.; Yamaguchi, R.
́
́
Organometallics 2006, 25, 4643−4647. (c) Corberan, R.; Sanau, M.;
Peris, E. Organometallics 2007, 26, 3492−3498. (d) Corberan, R.;
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