7 For reviews, see: (a) D. Prim, J.-M. Campagne, D. Joseph and B.
Andrioletti, Tetrahedron, 2002, 58, 2041–2075; (b) J. F. Hartwig, Angew.
Chem., Int. Ed., 1998, 37, 2046–2047; (c) I. P. Beletskaya and A. V.
Cheprakov, Coord. Chem. Rev., 2004, 248, 2337–2364; (d) J. P. Corbet
and G. Mignani, Chem. Rev., 2006, 106, 2651–2710.
W. B a o , J. Org. Chem., 2007, 72, 3863–3867; (n) N. Jiajai, H. Zhou, Z.
Li, J. Xu and S. Hu, J. Org. Chem., 2008, 73, 7814–7817; (o) F. Monnier
and M. Taillefer, Angew. Chem., Int. Ed., 2008, 47, 3096–3099; (p) Y.-H.
Liu, G. Li and L.-M. Yang, Tetrahedron Lett., 2009, 50, 343–346; (q) D.
Ma and Q. Cai, Org. Lett., 2003, 5, 3799–3802.
8 For Pd-catalyzed C–O(S) bond formation, see selected papers: (a) M.
Kosugi, T. Ogata, M. Terada, H. Sano and T. Migita, Bull. Chem.
Soc. Jpn., 1985, 58, 3657–3658; (b) M. J. Dickens, J. P. Gilday, T. J.
Mowlem and D. A. Widdowson, Tetrahedron, 1991, 47, 8621–8634;
(c) T. Ishiyama, M. Mori, A. Suzuki and N. Miyaura, J. Organomet.
Chem., 1996, 525, 225–231; (d) N. Zheng, J. C. McWilliams, F. J. Fleitz,
J. D. Armstrong and R. P. Volante, J. Org. Chem., 1998, 63, 9606–9607;
(e) G. Mann, D. Baranano, J. F. Hartwig, A. L. Rheingold and I. A.
Guzei, J. Am. Chem. Soc., 1998, 120, 9205–9213; (f) U. Schopfer and
A. Schlapbach, Tetrahedron, 2001, 57, 3069–3073; (g) G. Y. Li, Angew.
Chem., Int. Ed., 2001, 40, 1513–1516; (h) G. Y. Li, G. Zheng and A.
F. Noonan, J. Org. Chem., 2001, 66, 8677–8681; (i) M. Murata and
S. L. Buchwald, Tetrahedron, 2004, 60, 7397–7403; (j) T. Itoh and T.
Mase, Org. Lett., 2004, 6, 4587–4590; (k) C. Mispelaere-Canivet, J. F.
Spindler, S. Perrio and P. Beslin, Tetrahedron, 2005, 61, 5253–5259;
(l) M. A. Ferna´ndez-Rodr´ıguez, Q. Shen and J. F. Hartwig, Chem.–Eur.
J., 2006, 12, 7782–7796; (m) M. A. Ferna´ndez-Rodr´ıguez, Q. Shen and J.
F. Hartwig, J. Am. Chem. Soc., 2006, 128, 2180–2181; (n) R. S. Barbie´ri,
C. R. Bellato, A. K. C. Dias and C. Massabni, Catal. Lett., 2006, 109,
171–174; (o) J. S. Sawyer, Tetrahedron, 2000, 56, 5045–5065; (p) A. V.
Vorogushin, X. Huang and S. L. Buchwald, J. Am. Chem. Soc., 2005,
127, 8146–8149; (q) N. Kataoka, Q. Shelby, J. Stambuli and J. Hartwig,
J. Org. Chem., 2002, 67, 5553–5566; (r) M. Palucki, J. P. Wolfe and
S. L. Buchwald, J. Am. Chem. Soc., 1997, 119, 3395–3396; (s) X. Ku,
H. Huang, H. Jiang and H. Liu, J. Comb. Chem., 2009, 11, 338–340;
(t) M. Taillefer, N. Xia, and A. Ouali, US PATENT WO 2008/004088
A2.
9 For copper-catalyzed C–O coupling reactions, see: (a) J. Lindley, Tetra-
hedron, 1984, 40, 1433–1456; (b) S. Paul and M. Gupta, Tetrahedron
Lett., 2004, 45, 8825–8829; (c) J. F. Marcoux, S. Doye and S. L.
Buchwald, J. Am. Chem. Soc., 1997, 119, 10539–10540; (d) M. Wolter,
G. Nordmann, G. E. Job and S. L. Buchwald, Org. Lett., 2002, 4, 973–
976; (e) R. K. Gujadhur, C. G. Bates and D. Venkataraman, Org. Lett.,
2001, 3, 4315–4317; (f) R. K. Gujadhur and D. Venkataraman, Synth.
Commun., 2001, 31, 2865–2879; (g) E. Buck, Z. J. Song, D. Tschaen,
P. G. Dormer, R. P. Volante and P. J. Reider, Org. Lett., 2002, 4, 1623–
1626; (h) Y. J. Chen and H. H. Chen, Org. Lett., 2006, 8, 5609–5612;
(i) Y. Zhao, Y. Wang, H. Sun, L. Li and H. Zhang, Chem. Commun.,
2007, 3186–3188; (j) T. Miao and L. Wang, Tetrahedron Lett., 2007, 48,
95–99; (k) D. A. Evans, J. L. Katz and T. R. West, Tetrahedron Lett.,
1998, 39, 2937–2940; (l) H. J. A. Cristau, P. C. Pascal, S. Hamada, J. S.
Francis and M. Taillefer, Org. Lett., 2004, 6, 913–916; (m) X. Lv and
10 For general reviews, see: (a) C. Bolm, J. Legros, J. Le Paih and L. Zani,
Chem. Rev., 2004, 104, 6217–6254; (b) A. Fu¨rstner and R. Martin,
Chem. Lett., 2005, 34, 624–629; (c) Bernd Plietker in “Iron Catalysis
in Organic Chemistry”, Bernd Plietker Ed., 2008 WILEY-VCH Verlag,
Weinheim; (d) S. Enthaler, K. Junge and M. Beller, Angew. Chem., Int.
Ed., 2008, 47, 3317–3321; (e) A. Correa, O. Garcia Mancheno and C.
Bolm, Chem. Soc. Rev., 2008, 37, 1108–1117; (f) B. D. Sherry and A.
Fu¨rstner, Acc. Chem. Res., 2008, 41, 1500–1511; (g) W. M. Czaplik, M.
Mayer, J. Cvengros and A. Jacobi von Wangelin, ChemSusChem, 2009,
2, 396–417; (h) W. M. Czaplik, M. Mayer, S. Grupe and A. Jacobi von
Wangelin, Pure Appl. Chem., 2010, 82, 1545–1543; (i) C.-L. Sun, B.-J.
Li and Z.-J. Shi, Chem. Rev., 2011, 111, 1293–1314.
11 (a) M. Taillefer, N. Xia and A. Oualli, Angew. Chem., Int. Ed., 2007,
46, 934–936; (b) X.-F. Wu and C. Darcel, Eur. J. Org. Chem., 2009,
4753–4756; (c) D. Guo, H. Huang, Y. Zhou, J. Xu, H. Jiang, K. Chen
and H. Liu, Green Chem., 2010, 12, 276–281.
12 V. H. Jadhav, D. K. Dumbre, V. B. Phapale, H. B. Borate and R. D.
Wakharkar, Catal. Commun., 2007, 8, 65–68.
13 (a) A. Correa and C. Bolm, Angew. Chem., Int. Ed., 2007, 46, 8862–
8865; (b) A. Correa and C. Bolm, Adv. Synth. Catal., 2008, 350, 391–
394; (c) A. Correa, S. Elmore and C. Bolm, Chem.–Eur. J., 2008, 14,
3527–3529.
14 C–O coupling see: (a) O. Bistri, A. Correa and C. Bolm, Angew. Chem.,
Int. Ed., 2008, 47, 586–588; (b) N. Xia and M. Taillefer, Chem.–Eur. J.,
2008, 14, 6037–6039C–S coupling see: (c) A. Correa, M. Carril and C.
Bolm, Angew. Chem., Int. Ed., 2008, 47, 2880–2883.
15 (a) J. Mao, G. Xie, M. Wu, J. Guo and S. Ji, Adv. Synth. Catal., 2008, 350,
2477–2482; (b) H. Huang, H. Jiang, K. Chen and H. Liu, J. Org. Chem.,
2008, 73, 9061–9064; (c) C. M. R. Volla and P. Vogel, Tetrahedron Lett.,
2008, 49, 5961–5964; (d) S. L. Buchwald and C. Bolm, Angew. Chem.,
Int. Ed., 2009, 48, 5586–5587.
16 (a) G. Xie, P. Chellan, J. Mao, K. Chibale and G. S. Smith, Adv. Synth.
Catal., 2010, 352, 1641–1647; (b) J. Mao, Q. Hua, G. Xie, J. Guo, Z.
Yao, D. Shi and S. Ji, Adv. Synth. Catal., 2009, 351, 635–641; (c) J.
Mao, Q. Hua, J. Guo, Z. Yao and D. Shi, Eur. J. Org. Chem., 2009,
2262–2266; (d) Z. Xu, J. Mao and Y. Zhang, Catal. Commun., 2008, 9,
97–100; (e) J. Mao, Q. Hua, J. Guo, D. Shi and S. Ji, Synlett, 2008,
2011–2016.
17 CuI/KF/Al2O3 catalytic system for C–S couplings: Y.-S. Feng, Y.-Y. Li,
L. Tang, W. Wu and H.-J. Xu, Tetrahedron Lett., 2010, 51, 2489–2492.
18 L. K. Hwang, Y. Na, J. Lee, Y. Do and S. Chang, Angew. Chem., Int.
Ed., 2005, 44, 6166–6169.
5046 | Org. Biomol. Chem., 2011, 9, 5043–5046
This journal is
The Royal Society of Chemistry 2011
©