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’ REFERENCES
Zanotti-Gerosa, A.; Hancock, F.; Palin, E. J.; Catlow, C. R. A. Inorg.
Chem. 2008, 47, 2674. (g) Leyssens, T.; Peeters, D.; Harvey, J. N. Orga-
nometallics 2008, 27, 1514.
(12) (a) Abdur-Rashid, K.; Faatz, M.; Lough, A. J.; Morris, R. H.
J. Am. Chem. Soc. 2001, 123, 7473. (b) Hamilton, R. J.; Leong, C. G.;
Bigam, G.; Miskolzie, M.; Bergens, S. H. J. Am. Chem. Soc. 2005,
127, 4152. (c) Hamilton, R. J.; Bergens, S. H. J. Am. Chem. Soc. 2006,
128, 13700. (d) Hamilton, R. J.; Bergens, S. H. J. Am. Chem. Soc. 2008,
130, 11979.
(13) (a) Ito, M.; Hirakawa, M.; Murata, K.; Ikariya, T. Organometallics
2001, 20, 379. (b) Rautenstrauch, V.; Hoang-Cong, X.; Churland, R.;
Abdur-Rashid, K.; Morris, R. H. Chem.—Eur. J. 2003, 9, 4954. (c) Casey,
C. P.; Johnson, J. B.; Singer, S. W.; Cui, Q. J. Am. Chem. Soc. 2005,
127, 3100. (d) Hedberg, C.; K€allstr€om, K.; Arvidsson, P. I.; Brandt, P.;
Andersson, P. G. J. Am. Chem. Soc. 2005, 127, 15083. (e) Handgraaf, J.-W.;
Meijer, E. J. J. Am. Chem. Soc. 2007, 129, 3099.
(1) (a) Ohkuma, T.; Ooka, H.; Hashiguchi, S.; Ikariya, T.; Noyori, R.
J. Am. Chem. Soc. 1995, 117, 2675. (b) Noyori, R.; Ohkuma, T. Angew.
Chem., Int. Ed. 2001, 40, 40.(c) Handbook of Homogeneous Hydrogena-
tion; de Vries, J. G.; Elsevier, C. J., Eds.; Wiley-VCH: Weinheim,
Germany, 2007; Vol. 3, pp 1131ꢀ1163.
(2) (a) Ito, M.; Hirakawa, M.; Murata, K.; Ikariya, T. Organometallics
2001, 20, 379. (b) Ohkuma, T.; Koizumi, M.; Mu~niz, K.; Hilt, G.;
Kabuto, C.; Noyori, R. J. Am. Chem. Soc. 2002, 124, 6508. (c) Ohkuma,
T.; Utsumi, N.; Tsutsumi, K.; Murata, K.; Sandoval, C.; Noyori, R. J. Am.
Chem. Soc. 2006, 128, 8724. (d) Huang, H.; Okuno, T.; Tsuda, K.;
Yoshimura, M.; Kitamura, M. J. Am. Chem. Soc. 2006, 128, 8716.
(3) (a) Noyori, R.; Hashiguchi, S. Acc. Chem. Res. 1997, 30, 97. (b)
Ikariya, T.; Murata, K; Noyori, R. Org. Biomol. Chem. 2006, 4, 393. (c)
Malacea, R.; Poli, R.; Manoury, E. Coord. Chem. Rev. 2010, 254, 729.
(4) For recent publications, see: (a) Arai, N.; Suzuki, K.; Sugizaki, S.;
Sorimachi, H.; Ohkuma, T. Angew. Chem., Int. Ed. 2008, 47, 1770. (b)
Xie, J.-H.; Liu, S.; Kong, W.-L.; Bai, W.-J.; Wang, X.-C.; Wang, L.-X.;
Zhou, Q.-L. J. Am. Chem. Soc. 2009, 131, 4222.
(14) Haack, K.-J.; Hashiguchi, S.; Fujii, A.; Ikariya, T.; Noyori, R.
Angew. Chem., Int. Ed. Engl. 1997, 36, 258.
(15) (a) Casey, C. P.; Clark, T. B.; Guzei, I. A. J. Am. Chem. Soc. 2007,
129, 11821 and references therein. (b) Conley, B. L.; Pennington-Boggio,
M. K.; Boz, E.; Williams, T. J. Chem. Rev. 2010, 110, 2294.
(5) For recent publications, see: (a) Palmer, A. M.; Chiesa, V.; Holst,
H. C.; Le Paih, J.; Zanotti-Gerosa, A.; Nettekoven, U. Tetrahedron:
Asymmetry 2008, 19, 2102. (b) Zhang, J.; Blazecka, P. G.; Bruendl,
M. M.; Huang, Y. J. Org. Chem. 2009, 74, 1411.
ꢀ
(16) Samec, J. S. M.; Ell, A. H.; Åberg, J. B.; Privalov, T.; Eriksson, L.;
B€ackvall, J.-E. J. Am. Chem. Soc. 2006, 128, 14293.
(17) (a) Baratta, W.; Siega, K.; Rigo, P. Chem.—Eur. J. 2007, 13, 7479
and references therein. (b) Ayllꢀon, J. A.; Gervaux, C.; Sabo-Etienne, S.;
Chaudret, B. Organometallics 1997, 16, 2000.
(18) The yield of 1a was 70ꢀ80% when prepared under these con-
ditions. The remaining Ru species consisted of small amounts of decom-
position side products that formed during the steps required to prepare 1a
along with the Ru hydroxide compound trans-[Ru((R)-BINAP)-
(H)(OH)((R,R)-dpen)] formed from trace amounts of water.12c
(19) Olmstead, W. N.; Margolin, Z.; Bordwell, F. G. J. Org. Chem.
1980, 45, 3295.
(20) (a) Darensbourg, D. J.; Gr€otsch, G. J. Am. Chem. Soc. 1985,
107, 7473. (b) Darensbourg, D. J.; Hanckel, R. K.; Bauch, C. G.; Pala, M.;
Simmons, D.; White, J. N. J. Am. Chem. Soc. 1985, 107, 7463.
(21) (a) Whittlesey, M. K.; Perutz, R. N.; Moore, M. H. Organo-
metallics 1996, 15, 5516. (b) Jessop, P. G.; Hsiao, Y.; Ikariya, T.; Noyori,
R. J. Am. Chem. Soc. 1996, 118, 344. (c) Koike, T.; Ikariya, T. Adv. Synth.
Catal. 2004, 346, 37. (d) Urakawa, A.; Jutz, F.; Laurenczy, G.; Baiker, A.
Chem.—Eur. J. 2007, 13, 3886. (e) Getty, A. D.; Tai, C.-C.; Linehan,
J. C.; Jessop, P. G.; Olmstead, M. M.; Rheingold, A. L. Organometallics
2009, 28, 5466.
(6) (a) Ito, M.; Sakaguchi, A.; Kobayashi, C.; Ikariya, T. J. Am. Chem.
Soc. 2007, 129, 290. (b) Saudan, L.; Saudan, C. M.; Debieux, C.; Wyss, P.
Angew. Chem., Int. Ed. 2007, 46, 7473. (c) Ito, M.; Koo, L. W.; Himizu,
A.; Kobayashi, C.; Sakaguchi, A.; Ikariya, T. Angew. Chem., Int. Ed. 2009,
48, 1324. (d) Kuriyama, W.; Ino, Y.; Ogata, O.; Sayo, N.; Saito, T. Adv.
Synth. Catal. 2010, 352, 92. (e) Ito, M.; Kobayashi, C.; Himizu, A.;
Ikariya, T. J. Am. Chem. Soc. 2010, 132, 11414. (f) Takebayashi, S.;
Bergens, S. H. Organometallics 2009, 28, 2349. (g) Takebayashi, S.; John,
J. M.; Bergens, S. H. J. Am. Chem. Soc. 2010, 132, 12832. (h) Wylie,
W. N. O.; Lough, A. J.; Morris, R. H. Chem. Commun. 2010, 46, 8240. (i)
Ito, M.; Ootsuka, T.; Watari, R.; Shiibashi, A.; Himizu, A.; Ikariya, T.
J. Am. Chem. Soc. 2011, 133, 4240.
(7) (a) Casey, P. C.; Guan, H. J. Am. Chem. Soc. 2007, 129, 5816. (b)
Sui-Seng, C.; Freutel, F.; Lough, A. J.; Morris, R. H. Angew. Chem., Int.
Ed. 2008, 47, 940. (c) Mikhailine, A.; Lough, A. J.; Morris, R. H. J. Am.
Chem. Soc. 2009, 131, 1394. (d) Morris, R. H. Chem. Soc. Rev. 2009,
38, 2282. (e) Zhou, S.; Fleischer, S.; Junge, K.; Das, S.; Addis, D.; Beller,
M. Angew. Chem., Int. Ed. 2010, 49, 8121.
(8) Milstein recently reported Ru and Fe pincer complexes that
hydrogenate ketones, esters, or amides and proposed inner-coordina-
tion-sphere mechanisms. See: (a) Zhang, J.; Leitus, G.; Ben-David, Y.;
Milstein, D. Angew. Chem., Int. Ed. 2006, 45, 1113. (b) Balaraman, E.;
Gnanaprakasam, B.; Shimon, L. J. W.; Milstein, D. J. Am. Chem. Soc.
2010, 132, 16756. (c) Langer, L.; Leitus, G.; Ben-David, Y.; Milstein, D.
Angew. Chem., Int. Ed. 2011, 50, 2120.
(22) Vastine, B. A.; Hall, M. B. J. Am. Chem. Soc. 2007, 129, 12068
and references therein.
(9) (a) Casey, C. P.; Singer, S. W.; Powell, D. R.; Hayashi, R. K.;
Kavana, M. J. Am. Chem. Soc. 2001, 123, 1090. (b) Abdur-Rashid, K.;
Clapham, S. E.; Hadzovic, A.; Harvey, J. N.; Lough, A. J.; Morris, R. H.
J. Am. Chem. Soc. 2002, 124, 15104. (c) Casey, C. P.; Johnson, J. B. J. Org.
Chem. 2003, 68, 1998. (d) Sandoval, C. A.; Ohkuma, T.; Mu~niz, K.; Noyori,
ꢀ
R. J. Am. Chem. Soc. 2003, 125, 13490. (e) Samec, J. S. M.; Ell, A. H.;
B€ackvall, J.-E. Chem. Commun. 2004, 2748. (f) Casey, C. P.; Beetner, S. E.;
Johnson, J. B. J. Am. Chem. Soc. 2008, 130, 2285 and references therein. (g)
Iuliis, M. Z.-D.; Morris, R. H. J. Am. Chem. Soc. 2009, 131, 11263.
(10) Sandoval, C. A.; Yamaguchi, Y.; Ohkuma, T.; Kato, K.; Noyori,
R. Magn. Reson. Chem. 2006, 44, 66.
(11) (a) Alonso, D. A.; Brandt, P.; Nordin, S. J. M.; Andersson, P. G.
J. Am. Chem. Soc. 1999, 121, 9580. (b) Yamakawa, M.; Ito, H.; Noyori, R.
J. Am. Chem. Soc. 2000, 122, 1466. (c) Petra, D. G. I.; Reek, J. N. H.;
Handgraaf, J.-W.; Meijer, E. J.; Dierkes, P.; Kamer, P. C. J.; Brussee, J.;
Schoemaker, H. E.; van Leeuwen, P. W. N. M. Chem.—Eur. J. 2000,
6, 2818. (d) Comas-Vives, A.; Ujaque, G.; Lledꢀos, A. Organometallics
2007, 26, 4135. (e) Hadzovic, A.; Song, D.; MacLaughlin, C. M.; Morris,
R. H. Organometallics 2007, 26, 5987. (f) Tommaso, D. D.; French, S. A.;
9669
dx.doi.org/10.1021/ja202732q |J. Am. Chem. Soc. 2011, 133, 9666–9669