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(n) Sherden, N. H.; Behenna, D. C.; Virgil, S. C.; Stoltz, B. M. Angew.
Chem., Int. Ed. 2009, 48, 6840–6843. (o) Caldentey, X.; Pericꢀas, M. A.
J. Org. Chem. 2010, 75, 2628–2644. (p) Liu, W.-B.; He, H.; Dai, L.-X.;
You, S.-L. Chem.—Eur. J. 2010, 16, 7376–7379. (q) Weaver, J. D.; Ka,
B. J.; Morris, D. K.; Thompson, W.; Tunge, J. A. J. Am. Chem. Soc. 2010,
132, 12179–12181. (r) Grenning, A. J.; Tunge, J. A. Angew. Chem., Int. Ed.
2011, 50, 1688–1691. (s) Chen, J.-P.; Peng, Q.; Lei, B.-L.; Hou, X.-L.;
Wu, Y.-D. J. Am. Chem. Soc. 2011, 133, 14180–14183. (t) Grenning, A. J.;
Tunge, J. A. J. Am. Chem. Soc. 2011, 133, 14785–14794. (u) Mukherjee,
H.; McDougal, N. T.; Virgil, S. C.; Stoltz, B. M. Org. Lett. 2011, 13,
825–827.
’ AUTHOR INFORMATION
Corresponding Author
Author Contributions
§These authors contributed equally.
(4) (a) Hirao, T.; Yamada, N.; Ohshiro, Y.; Agawa, T. J. Organomet.
Chem. 1982, 236, 409–414. (b) Yamamoto, T.; Akimoto, M.; Saito, O.;
Yamamoto, A. Organometallics 1986, 5, 1559–1567.
(5) (a) Murahashi, S.-I.; Makabe, Y. Tetrahedron Lett. 1985, 26,
5563–5566. (b) Murahashi, S.-I.; Makabe, Y.; Kunita, K. J. Org. Chem.
1988, 53, 4489–4495.
(6) Mukherjee, S.; List, B. J. Am. Chem. Soc. 2007, 129, 11336–11337.
(7) (a) Watson, I. D. G.; Yudin, A. K. J. Am. Chem. Soc. 2005,
127, 17516–17529. (b) Dubovyk, I.; Pichugin, D.; Yudin, A. K. Angew.
Chem., Int. Ed. 2011, 50, 5924–5926.
’ ACKNOWLEDGMENT
This work was supported by the National Nature Science
Foundation of China (No. 20972095 and 21172143), Science
and Technology Commission of Shanghai Municipality (No.
10dz1910105), and Nippon Chemical Industrial Co., Ltd. We
thank Prof. Tsuneo Imamoto and Dr. Masashi Sugiya for helpful
discussions.
(8) (a) Trost, B. M.; Osipov, M.; Dong, G. J. Am. Chem. Soc. 2010,
132, 15800–15807. (b) Lowe, M. A.; Ostovar, M.; Ferrini, S.; Chen,
C. C.; Lawrence, P. G.; Fontana, F.; Calabrese, A. A.; Aggarwal, V. K.
Angew. Chem., Int. Ed. 2011, 50, 6370–6374.
(9) Bao, H.; Qi, X.; Tambar, U. K. J. Am. Chem. Soc. 2011, 133,
1206–1208.
(10) Zhao, X.; Liu, D.; Liu, Y.; Zhang, W. Org. Biomol. Chem. 2011,
9, 1871–1875.
(11) McMurry, J. E. Organic Chemistry, 6th ed.; Brooks/Cole:
’ REFERENCES
(1) (a) Metallo-organic Chemistry; Pearson, A. J., Ed.; John Wiley &
Sons: New York, 1985. (b) Wulff, W. D. In Advances in Metal-Organic
Chemistry; Liebeskind, L. S., Ed.; Jai Press: London, 1989; Vol. 1.
(c) Metal-catalyzed Cross-coupling Reactions; Diederich, F., Stang, P. J.,
Eds.; Wiley-VCH: Weinheim, 1998. (d) Beller, M., Zapf, A. In Handbook
of Organopalladium Chemistry for Organic Synthesis; Negishi, E.-I., Ed.;
Wiley: New York, 2002; Vol. 1. (e) Metal-Catalyzed Cross-Coupling
Reactions, 2nd ed.; de Meijere, A., Diederich, F., Eds.; Wiley-VCH:
Weinheim, 2004; Vols. 1 and 2. (f) Dubbaka, S. R.; Vogel, P. Angew.
Chem., Int. Ed. 2005, 44, 7674–7684. (g) Yamamoto, Y.; Hattori, K.;
Nishiyama, H. J. Am. Chem. Soc. 2006, 128, 8336–8340. (h) Alberico, D.;
Scott, M. E.; Lautens, M. Chem. Rev. 2007, 107, 174–238. (i) Singh, B. K.;
Kaval, N.; Tomar, S.; Eycken, E. V. D.; Parmar, V. S. Org. Process Res. Dev.
2008, 12, 468–474. (j) Watson, I. D. G.; Ritter, S.; Toste, F. D.
J. Am. Chem. Soc. 2009, 131, 2056–2057. (k) Park, J. W.; Jun, C. H. J. Am.
Chem. Soc. 2010, 132, 7268–7269.
(2) Selected reviews: (a) Trost, B. M.; van Vranken, D. L. Chem. Rev.
1996, 96, 395–422. (b) Pfaltz, A.; Lautens, M. In Comprehensive
Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.;
Springer: New York, 1999; Vol. 2. (c) Trost, B. M.; Crawley, M. L. Chem.
Rev. 2003, 103, 2921–2943. (d) Yorimitsu, H.; Oshima, K. Angew. Chem.,
Int. Ed. 2005, 44, 4435–4439. (e) You, S. L.; Dai, L. X. Angew. Chem., Int.
Ed. 2006, 45, 5246–5248. (f) Braun, M.; Meier, T. Angew. Chem., Int. Ed.
2006, 45, 6952–6955. (g) Zhan, L.; Ma, S. Angew. Chem., Int. Ed. 2008,
47, 258–297. (h) Weaver, J. D.; Recio, A., III; Grenning, A. J.; Tunge, J. A.
Chem. Rev. 2011, 111, 1846–1913. (i) Zhang, W.; Liu, D. In Chiral
Ferrocenes in Asymmetric Catalysis: Synthesis and Applications; Dai, L. X.,
Hou, X. L., Eds.; Wiley-VCH: Weinheim, 2010; Chapter 14.
Belmont, CA, 2003.
(12) The reaction did not occur with polar aprotic solvents such as
THF, CH2Cl2, CH3CN, CH3NO2, DMF, DMSO, and NMP.
(13) Details are shown in the Supporting Information.
(14) (a) Whalley, E.; Falk, M. J. Chem. Phys. 1961, 34, 1569–1571.
(b) England-Kretzer, L.; Luck, W. A. P. J. Mol. Struct. 1995,
348, 373–376. (c) Ludwig, R. In NIC Symposium 2004, Proceedings;
Wolf, D., M€unster, G., Kremer, M., Eds.; NIC Series, 2003; Vol. 20, pp
61À70.
(15) Zhang, W.; Adachi, Y.; Hirao, T.; Ikeda, I. Tetrahedron:
Asymmetry 1996, 7, 451–460.
(3) Selected papers using -OAc or -OCO2R as leaving group:
(a) Steinhagen, H.; Reggelin, M.; Helmchen, G. Angew. Chem., Int. Ed.
1997, 36, 2108–2110. (b) Zhang, W.; Shimanuki, T.; Kida, T.; Nakatsuji,
Y.; Ikeda, I. J. Org. Chem. 1999, 64, 6247–6251. (c) Weiss, T. D.; Helmchen,
G.; Kazmaier, U. Chem. Commun. 2002, 1270–1271. (d) Oohara, N.;
Katagiri, K.; Imamoto, T. Tetrahedron: Asymmetry 2003, 14, 2171–2175.
(e) Hayashi, T.; Suzuka, T.; Okada, A.; Kawatsura, M. Tetrahedron:
Asymmetry 2004, 15, 545–548. (f) Shintani, R.; Duan, W.-L.; Hayashi, T.
J. Am. Chem. Soc. 2006, 128, 5628–5629. (g) Markert, C.; Neuburger,
M.; Kulicke, K.; Meuwly, M.; Pfaltz, A. Angew. Chem., Int. Ed. 2007,
46, 5892–5895. (h) Liu, D.; Xie, F.; Zhang, W. J. Org. Chem. 2007,
72, 6992–6997. (i) Liu, D.; Xie, F.; Zhang, W. Tetrahedron Lett. 2007,
48, 585–588. (j) Liu, D.; Xie, F.; Zhang, W. Tetrahedron Lett. 2008,
49, 1012–1015. (k) Zhao, X.; Liu, D.; Xie, F.; Zhang, W. Tetrahedron
2009, 65, 512–517. (l) Liu, W.; Chen, D.; Zhu, X.-Z.; Wan, X.-L.;
Hou, X.-L. J. Am. Chem. Soc. 2009, 131, 8734–8735. (m) He, H.; Liu,
W.-B.; Dai, L.-X.; You, S.-L. J. Am. Chem. Soc. 2009, 131, 8346–8347.
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