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Article
(5) Jacobsen, E. N.; Markd, I.; Schrcider, G.; Sharpless, K. B. J. Am.
Chem. Soc. 1988, 110, 1968−1970.
(39) (a) Pidun, U.; Boehme, C.; Frenking, G. Angew. Chem., Int. Ed.
Engl. 1996, 35, 2817−2820. (b) Dapprich, S.; Ujaque, G.; Maseras, F.;
(6) Minoto, M.; Yamamoto, K.; Tsuji, J. J. Org. Chem. 1990, 55, 766−
768.
́
Lledos, A.; Musaev, D. G.; Morokuma, K. J. Am. Chem. Soc. 1996, 118,
11660−11661. (c) Haller, J.; Strassner, T.; Houk, K. N. J. Am. Chem.
Soc. 1997, 119, 8031−8034. (d) Delmonte, A. J.; Haller, J.; Houk, K.
N.; Sharpless, K. B.; Singleton, D. A.; Strassner, T.; Thomas, A. A. J.
Am. Chem. Soc. 1997, 119, 9907−9908.
(7) Kobayashi, S.; Endo, M.; Nagayama, S. J. Am. Chem. Soc. 1999,
121, 11229−11230.
(8) Kobayashi, S.; Ishida, T.; Akiyama, R. Org. Lett. 2001, 3, 2649−
2652.
(9) Severeyns, A.; Vos, D. E. E.; Fiermans, L.; Verpoort, F.; Grobet,
P. J.; Jacobs, P. A. Angew. Chem., Int. Ed. 2001, 40, 586−589.
(10) Yao, Q. Org. Lett. 2002, 4, 2197−2199.
(11) Bataille, C. J. R.; Donohoe, T. J. Chem. Soc. Rev. 2011, 40, 114−
118.
(40) Nova, A.; Ujaque, G.; Maseras, F.; Lledos
Chem. Soc. 2006, 128, 14571−14578.
́
, A.; Espinet, P. J. Am.
(41) (a) Goossen, L. J.; Koley, D.; Hermann, H. L.; Thiel, W. J. Am.
Chem. Soc. 2005, 127, 11102−11114. (b) Goossen, L. J.; Koley, D.;
Hermann, H. L.; Thiel, W. Organometallics 2006, 25, 54−67.
́
́
(c) Alvarez, R.; Faza, O. N.; Lopez, C. S.; de Lera, A. R. Org. Lett.
́
(12) Fujita, M.; Costas, M.; Que, L., Jr. J. Am. Chem. Soc. 2003, 125,
2006, 8, 35−38. (d) Hicks, J. D.; Hyde, A. M.; Cuezva, A. M.;
Buchwald, S. L. J. Am. Chem. Soc. 2009, 131, 16720−16734.
(42) Ariafard, A.; Yates, B. F. J. Am. Chem. Soc. 2009, 131, 13981−
13991.
9912−9913.
(13) De Boer, J. W.; Brinksma, J.; Browne, W. R.; Meetsma, A.;
Alsters, P. L.; Hage, R.; Feringa, B. L. J. Am. Chem. Soc. 2005, 127,
7990−7991.
(43) Surawatanawong, P.; Hall, M. B. Organometallics 2008, 27,
(14) Suzuki, K.; Oldenbug, P. D.; Que, L., Jr. Angew. Chem., Int. Ed.
2008, 47, 1887−1889.
(15) Bruijnincx, P. C. A.; Buurmans, I. L. C.; Gosiewska, S.;
Moelands, M. A. H.; Lutz, M.; Spek, A. L.; Koten, G.; Gebbink, R. J.
M. K. Chem.-Eur. J. 2008, 14, 1228−1237.
(16) Oldenburg, P. D.; Geng, Y.; Pryjomska-Ray, I.; Ness, D.; Que,
L., Jr. J. Am. Chem. Soc. 2010, 132, 17713−17723.
(17) Chow, T. W-A.; Wong, E. L.-M.; Guo, Z.; Liu, Y.; Huang, J.-S.;
Che, C.-M. J. Am. Chem. Soc. 2010, 132, 13229−13239.
(18) Yip, W.-P.; Ho, C.-M.; Zhu, N.; Lau, T.-C.; Che, C.-M. Chem.-
Asian J. 2008, 3, 70−77.
6222−6232.
(44) Lan, Y.; Wang, C.; Sowa, J. R.; Wu, Y.-D. J. Org. Chem. 2010, 75,
951−954.
(45) Maestri, G.; Motti, E.; Della Ca’, N.; Malacria, M.; Derat, E.;
Catellani, M. J. Am. Chem. Soc. 2011, 133, 8574−8585.
(46) Hay, P. J.; Wadt, W. R. J. Chem. Phys. 1985, 82, 299−310.
(47) (a) Fukui, K. J. Phys. Chem. 1970, 74, 4161−4163. (b) Fukui, K.
Acc. Chem. Res. 1981, 14, 363−368.
(48) (a) Gonzalez, C.; Schlegel, H. B. J. Chem. Phys. 1989, 90, 2154−
2161. (b) Gonzalez, C.; Schlegel, H. B. J. Phys. Chem. 1990, 94, 5523−
5527.
(49) (a) Hratchian, H. P.; Schlegel, H. B. J. Chem. Phys. 2004, 120,
9918−9924. (b) Hratchian, H. P.; Schlegel, H. B. J. Chem. Theory
Comput. 2005, 1, 61−69.
(50) Dolg, M.; Wedig, U.; Stoll, H.; Preuss, H. J. Chem. Phys. 1987,
86, 866−872.
(19) Milas, N. A.; Sussman, S. J. Am. Chem. Soc. 1936, 58, 1302−
1304.
(20) Milas, N. A.; Sussman, S. J. Am. Chem. Soc. 1937, 59, 2345−
2347.
(21) Milas, N. A.; Sussman, S.; Mason, H. S. J. Am. Chem. Soc. 1939,
61, 1844−1847.
(51) (a) Wachters, A. J. H. J. Chem. Phys. 1970, 52, 1033−1036.
(b) Hay, P. J. J. Chem. Phys. 1977, 66, 4377−4384. (c) Trucks, G. W.;
Raghavachari, K. J. Chem. Phys. 1989, 91, 1062−1065.
(52) Grimme, S. J. Comput. Chem. 2006, 27, 1787−1799.
(53) (a) Zhao, Y.; Truhlar, D. G. Theor. Chem. Acc. 2008, 120, 215−
241. (b) Zhao, Y.; Truhlar, D. G. Acc. Chem. Res. 2008, 41, 157−167.
(54) (a) Takahara, Y.; Fueno, T.; Yamaguchi, K. Chem. Phys. Lett.
1989, 157, 211−216. (b) Yamaguchi, K.; Okumura, M.; Mori, W.;
Maki, J.; Takada, K.; Noro, T.; Tanaka, K. Chem. Phys. Lett. 1993, 210,
201−210. (c) Kitagawa, Y.; Saito, T.; Ito, M.; Shoji, M.; Koizumi, K.;
Yamanaka, S.; Kawakami, T.; Okumura, M.; Yamaguchi, K. Chem.
Phys. Lett. 2007, 442, 445−450.
(22) Milas, N. A.; Trepagnier, J. H.; Nolan, J. T., Jr.; Iliopulos, M. I. J.
Am. Chem. Soc. 1959, 81, 4730−4733.
(23) Begstad, K.; Jonsson, S. Y.; Backvall, J.-E. J. Am. Chem. Soc.
̈
1999, 121, 10424−10425.
(24) Jonsson, S. Y.; Farnegardh, K.; Backvall, J.-E. J. Am. Chem. Soc.
̈
̈
2001, 123, 1365−1371.
(25) Dobson, J. C.; Takeuchi, K. J.; Pipes, D. W.; Geselowitz, D. A.;
Meyer, T. J. Inorg. Chem. 1986, 25, 2357−2365.
(26) Pipes, D. W.; Meyer, T. J. Inorg. Chem. 1986, 25, 4042−4050.
(27) Kober, E. M.; Caspar, J. V.; Sullivan, B. P.; Meyer, T. J. Inorg.
Chem. 1988, 27, 4587−4598.
(28) Dobson, J. C.; Meyer, T. J. Inorg. Chem. 1989, 28, 2013−2016.
(55) Reed, A. E.; Weinhold, F. J. Chem. Phys. 1985, 83, 1736−1740.
́
(29) Costentin, C.; Robert, M.; Save ant1, J. M.; Teillout, A. L. Proc.
̌
(56) (a) Miertus, S.; Scrocco, E.; Tomasi, J. Chem. Phys. 1981, 5,
Natl. Acad. Sci. U.S.A. 2009, 106, 11829−11836.
117−129. (b) Tomasi, J.; Mennucci, B.; Cammi, R. Chem. Rev. 2005,
105, 2999−3093.
(30) Che, C.-M.; Yam, V. W. W.; Cho, K. C.; Gray, H. B. J. Chem.
Soc., Chem. Commun. 1987, 948−949.
(57) Scalmani, G.; Frisch, M. J. J. Chem. Phys. 2010, 132, 114110.
(58) Chantooni, M. K., Jr.; Kolthoff, I. M. Anal. Chem. 1979, 51,
133−140.
(31) Schindler, S.; Castner, E. W., Jr.; Creutz, C.; Sutin, N. Inorg.
Chem. 1993, 32, 4200−4208.
(32) Chin, K. F.; Cheng, Y. K.; Cheung, K. K.; Guo, C. X.; Che, C.-
M. J. Chem. Soc., Dalton Trans. 1995, 2967−2973.
(33) Cheng, J. Y. K.; Cheung, K. K.; Che, C. M.; Lau, T. C. Chem.
Commun. 1997, 1443−1444.
(59) Sugimoto, H.; Matsunami, C.; Koshi, C.; Yamasaki, M.;
Umakoshi, K.; Sasaki, Y. Bull. Chem. Soc. Jpn. 2001, 74, 2091−2099.
(60) The catalytic dihydroxylation of cyclohexene was carried out in
water without acetate buffer, where the yield of diol was 70%. Excellent
yields were also obtained at pH 6.0 and 8.0 in the KH2PO4−Na2HPO4
buffer solutions (Table S2). These results unambiguously indicate that
peracetic acid formation was not required in the present catalytic
system. The somewhat lower yield (70%) in water as compared to the
yield in the buffer solutions may be attributed to unstable pH
conditions in water. As clearly shown in Table S2 and Figure 3, pH
control is critical in the present catalytic reaction.
(34) Sugimoto, H.; Kitayama, K.; Ashikari, K.; Matsunami, C.; Ueda,
N.; Umakoshi, K.; Hosokoshi, Y.; Sasaki, Y.; Itoh, S. Inorg. Chem.
2011, 50, 9014−9023.
(35) Burla, M. C.; Caliandro, R.; Camalli, M.; Carrozzini, B.;
Cascarano, G. L.; De Caro, L.; Giacovazzo, C.; Polidori, G.; Siliqi, D.;
Spagna, R. SIR2008; 2007.
(36) Crystal Structure 3.8: Crystal Structure Analysis Package; Rigaku
Corp.: The Woodlands, TX, 2000−2006.
(37) Frisch, M. J.; et al. Gaussian 09, revision C.01; Gaussian, Inc.:
Wallingford, CT, 2009.
(38) (a) Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785−
789. (b) Becke, A. D. J. Chem. Phys. 1993, 98, 5648−5652.
(61) No distinctive intermediate such as OsIII−OOH was detected in
the direct reaction of 2 or 3 with H2O2 by UV−vis, resonance Raman,
and ESI−MS spectral methods under the experimental conditions
employed.
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dx.doi.org/10.1021/ja309566c | J. Am. Chem. Soc. 2012, 134, 19270−19280