3 (a) R. Chinchilla and C. Najera, Chem. Rev., 2007, 107, 874–922; (b) H.
Doucet and J.-C. Hierso, Angew. Chem., Int. Ed., 2007, 46, 834–871;
(c) H. Plenio, Angew. Chem., Int. Ed., 2008, 47, 6954–6956.
4 For papers on the Sonogashira cross-coupling reaction catalyzed by
a catalytic amount of copper, see: (a) K. Okuro, M. Furuune, M.
Enna, M. Miura and M. Nomura, J. Org. Chem., 1993, 58, 4716–
4721; (b) R. K. Gujadhur, C. G. Bates and D. Venkataraman, Org.
Lett., 2001, 3, 4315–4317; (c) D. Ma and F. Liu, Chem. Commun.,
2004, 1934–1935; (d) P. Saejueng, C. G. Bates and D. Venkataraman,
Synthesis, 2005, 1706–1712; (e) Y.-X. Xie, C.-L. Deng, S.-F. Pi, J.-H.
Li and D.-L. Yin, Chin. J. Chem., 2006, 24, 1290–1294; (f) S.-M. Guo,
C.-L. Deng and J.-H. Li, Chin. Chem. Lett., 2007, 18, 13–18; (g) J.-H.
Li, J.-L. Li, D.-P. Wang, S.-F. Pi, Y.-X. Xie, M.-B. Zhang and X.-C. Hu,
J. Org. Chem., 2007, 72, 2053–2057; (h) J.-H. Li, J.-L. Li and Y.-X. Xie,
Synthesis, 2007, 984–988.
Brochu, N. Guimond, K. H. Thesen and P. Forginone, J. Org. Chem.,
2010, 75, 1550–1560.
13 (a) J. Moon, M. Jeong, H. Nam, J. Ju, J. H. Moon, H. M. Jung and S.
Lee, Org. Lett., 2008, 10, 945–948; (b) J. Moon, M. Jang and S. Lee,
J. Org. Chem., 2009, 74, 1403–1406; (c) H. Kim and P. H. Lee, Adv.
Synth. Catal., 2009, 351, 2827–2832; (d) W.-W. Zhang, X.-G. Zhang
and J.-H. Li, J. Org. Chem., 2010, 75, 5259–5264; (e) K. Park, G. Bae, J.
Moon, J. Choe, K. H. Song and S. Lee, J. Org. Chem., 2010, 75, 6244–
6251; (f) C. Feng and T.-P. Loh, Chem. Commun., 2010, 46, 4779–4781;
(g) S. Ranjit, Z. Duan, P. Zhang and X. Liu, Org. Lett., 2010, 12, 4134–
4136; (h) M. Yu, D. Pan, W. Jia, W. Chen and N. Jiao, Tetrahedron
Lett., 2010, 51, 1287–1290; (i) W. Jia and N. Jiao, Org. Lett., 2010, 12,
2000–2003.
14 (a) G. Xie, P. Chellan, J. Mao, K. Chibale and G. S. Smith, Adv. Synth.
Catal., 2010, 352, 1641–1647; (b) J. Mao, G. Xie, J. Zhan, Q. Hua and
D. Shi, Adv. Synth. Catal., 2009, 351, 1268–1272; (c) J. Mao, Q. Hua,
G. Xie, J. Guo, Z. Yao, D Shi and S. Ji, Adv. Synth. Catal., 2009, 351,
635–641; (d) J. Mao, G. Xie, M. Wu, J. Guo and S. Ji, Adv. Synth. Catal.,
2008, 350, 2477–2482; (e) J. Mao, Q. Hua, J. Guo, Z. Yao and D. Shi,
Eur. J. Org. Chem., 2009, 2262–2266.
15 R. Shang, Y. Fu, Y. Wang, Q. Xu, H.-Z. Yu and L. Liu, Angew. Chem.,
Int. Ed., 2009, 48, 9350–9355.
16 D. Zhao, C. Gao, X. Su, Y. He, J. You and Y. Xue, Chem. Commun.,
2010, 46, 9049–9051.
17 We are grateful for the reviewers who gave us some good advice.
18 (a) K. Okuro, M. Furuune, M. Ema, M. Miura and M. Nomura, J. Org.
Chem., 1993, 58, 4716–4721; (b) L. Ray, S. Barman, M. M. Shaikh
and P. Ghosh, Chem.–Eur. J., 2008, 14, 6646–6655; (c) Z. Gonda,
G. L. Tolnai and Z. Nova´k, Chem.–Eur. J., 2010, 16, 11822–11826;
(d) T. Lauterbach, M. Livendahl, A. Rosello´n, P. Espinet and A. M.
Echavarren, Org. Lett., 2010, 12, 3006–3009.
5 M. Carril, A. Correa and C. Bolm, Angew. Chem., Int. Ed., 2008, 47,
4862–4865.
6 A. Corma, C. Gonza´lez-Arellano, M. Iglesias and F. Sa´nchez, Angew.
Chem., Int. Ed., 2007, 46, 7820–7822.
7 H. N. Borah, D. Prajapati and R. C. Boruah, Synlett, 2005, 2823–2825.
8 L. Wang, P. Li and Y. Zhang, Chem. Commun., 2004, 514–515.
9 L. Feng, F. Liu, P. Sun and J. Bao, Synlett, 2008, 1415–1417.
10 S. Park, M. Kim, D. H. Koo and S. Chang, Adv. Synth. Catal., 2004,
346, 1638–1640.
11 J. Mao, M. Wu, G. Xie and S. Ji, Adv. Synth. Catal., 2009, 351, 2101–
2106.
12 (a) L. J. Goossen, N. Rodr´ıguez and K. Goossen, Angew. Chem., Int.
Ed., 2008, 47, 3100–3120; (b) S.-L. You and L.-X. Dai, Angew. Chem.,
Int. Ed., 2006, 45, 5246–5248; (c) D. Tanaka, S. P. Romeril and A. G.
Myers, J. Am. Chem. Soc., 2005, 127, 10323–10337; (d) F. Zhang and
M. F. Greaney, Org. Lett., 2010, 12, 4745–4747; (e) F. Bilodeau, M.-C.
6942 | Org. Biomol. Chem., 2011, 9, 6938–6942
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