4292
S. Yang et al. / Tetrahedron Letters 53 (2012) 4288–4292
Am. Chem. Soc. 2008, 130, 6586–6596; (g) Su, M.; Buchwald, S. L. Angew. Chem.,
Int. Ed. 2012, 51, 4710–4713.
and freshly distilled anhydrous DMSO should be the optimal
choice.
7. For C–O, please see: (a) Tlili, A.; Monnier, F.; Taillefer, M. Chem. Eur. J. 2010, 16,
12299–12302; (b) Niu, J.; Zhou, H.; Li, Z.; Xu, J.; Hu, S. J. Org. Chem. 2008, 73,
7814–7817; (c) Gujadhur, R. K.; Bates, C. G.; Venkataraman, D. Org. Lett. 2001, 3,
4315–4317; (d) Chen, Y.-J.; Chen, H.-H. Org. Lett. 2006, 8, 5609–5612; (e) Ma,
D.; Cai, Q. Org. Lett. 2003, 5, 3799–3802; (f) Lv, X.; Bao, W. J. Org. Chem. 2007, 72,
3863–3867; (g) Ouali, A.; Spindler, J.-F.; Jutand, A.; Taillefer, M. Adv. Synth.
Catal. 2007, 349, 1906–1916; (h) Cristau, H.-J.; Cellier, P. P.; Hamada, S.;
Spindler, J.-F.; Taillefer, M. Org. Lett. 2004, 6, 913–916; (i) Buck, E.; Song, Z. J.;
Tschaen, D.; Dormer, P. G.; Volante, R. P.; Reider, P. J. Org. Lett. 2002, 4, 1623–
1626; (j) Naidu, A. B.; Jaseer, E. A.; Sekar, G. J. Org. Chem. 2009, 74, 3675–3679;
(k) Zhang, Q.; Wang, D.; Wang, X.; Ding, K. J. Org. Chem. 2009, 74, 7187–7190;
(l) Miao, T.; Wang, L. Tetrahedron Lett. 2007, 48, 95–99; For N-aryl imidazoles,
please see: (m) Liang, L.; Li, Z.; Zhou, X. Org. Lett. 2009, 11, 3294–3297; (n) Li,
X.; Yang, D.; Jiang, Y.; Fu, H. Green Chem. 2010, 12, 1097–1105; (o) Wang, D.;
Zhang, F.; Kuang, D.; Yu, J.; Li, J. Green Chem. 2012, 14, 1268–1271.
8. Arundhathi, R.; Damodara, D.; Likhar, P. R.; Kantam, M. L.; Saravanan, P.;
Magdaleno, T.; Kwon, S. H. Adv. Synth. Catal. 2011, 353, 1591–1600.
9. Kim, H. J.; Kim, M.; Chang, S. Org. Lett. 2011, 13, 2368–2371.
Acknowledgments
We are grateful to the State Key Laboratory of Electroanalytical
Chemistry for financial support.
Supplementary data
Supplementary data associated with this article can be found, in
131. These data include MOL files and InChiKeys of the most
important compounds described in this article.
10. (a) Sawyer, J. S.; Schmittling, E. A.; Palkowitz, J. A.; Smith, W. J. J. Org. Chem.
1998, 63, 6338–6343; (b) Jalalian, N.; Ishikawa, E. E.; Silva, L. F.; Olofsson, B.
Org. Lett. 2011, 13, 1552–1555; (c) Liu, Z.; Larock, R. C. Org. Lett. 2003, 6, 99–
102; (d) Liu, Z.; Larock, R. C. J. Org. Chem. 2006, 71, 3198–3209; (e) Khalilzadeh,
M. A.; Hosseini, A.; Pilevar, A. Eur. J. Org. Chem. 2011, 2011, 1587–1592.
11. Yuan, Y.; Thomé, I.; Kim, S. H.; Chen, D.; Beyer, A.; Bonnamour, J.; Zuidema, E.;
Chang, S.; Bolm, C. Adv. Synth. Catal. 2010, 352, 2892–2898.
12. Cano, R.; Ramo´n, D. J.; Yus, M. J. Org. Chem. 2010, 76, 654–660.
13. t-BuOK (P97.0% purity, Aldrich Co., product number 60098) was used as
received. Its ICP-OES analysis showed that the contents of Au, Ag, Al, Fe, Ca, Cd,
Cu, Cr, Rh, Pd, Ir, Pt and Mg are below the detection limit. The content of Co is
2.5 ppm, which is unlikely to be a promoter for the present coupling reaction.
14. Narayan, S.; Muldoon, J.; Finn, M. G.; Fokin, V. V.; Kolb, H. C.; Sharpless, K. B.
Angew. Chem., Int. Ed. 2005, 44, 3275–3279.
15. For transition metal catalizes Ullmann C–O couping reaction, the order of
reactivity is I > Br. However, if through benzyne, the order is Br > I. For details,
please see: Bradshaw, J. S.; Hales, R. H.; Pratt, D. R. J. Org. Chem. 1971, 36, 314–
318.
16. (a) Yanagisawa, S.; Ueda, K.; Taniguchi, T.; Itami, K. Org. Lett. 2008, 10, 4673–
4676; (b) Sun, C.-L.; Li, H.; Yu, D.-G.; Yu, M.; Zhou, X.; Lu, X.-Y.; Huang, K.;
Zheng, S.-F.; Li, B.-J.; Shi, Z.-J. Nat. Chem. 2010, 2, 1044–1049; (c) Liu, W.; Cao,
H.; Zhang, H.; Zhang, H.; Chung, K. H.; He, C.; Wang, H.; Kwong, F. Y.; Lei, A. J.
Am. Chem. Soc. 2010, 132, 16737–16740; (d) Shirakawa, E.; Zhang, X.; Hayashi,
T. Angew. Chem., Int. Ed. 2011, 50, 4671–4674.
References and notes
1. (a) Beletskaya, I.; Cheprakov, A. Coord. Chem. Rev. 2004, 248, 2337–2364; (b)
Ley, S. V.; Thomas, A. W. Angew. Chem., Int. Ed. 2003, 42, 5400–5449; (c)
Monnier, F.; Taillefer, M. Angew. Chem., Int. Ed. 2008, 47, 3096–3099; (d) Correa,
A.; García Mancheño, O.; Bolm, C. Chem. Soc. Rev. 2008, 37, 1108–1117; (e)
Wang, Y.; Wu, Z.; Wang, L.; Li, Z.; Zhou, X. Chem. Eur. J. 2009, 15, 8971–8974.
2. (a) Nicolaou, K. C.; Natarajan, S.; Li, H.; Jain, N. F.; Hughes, R.; Solomon, M. E.;
Ramanjulu, J. M.; Boddy, C. N. C.; Takayanagi, M. Angew. Chem., Int. Ed. 1998, 37,
2708–2714; (b) Evans, D. A.; Dinsmore, C. J.; Watson, P. S.; Wood, M. R.;
Richardson, T. I.; Trotter, B. W.; Katz, J. L. Angew. Chem., Int. Ed. 1998, 37, 2704–
2708.
3. Deng, H.; Jung, J.-K.; Liu, T.; Kuntz, K. W.; Snapper, M. L.; Hoveyda, A. H. J. Am.
Chem. Soc. 2003, 125, 9032–9034.
4. (a) Uchiro, H.; Kato, R.; Arai, Y.; Hasegawa, M.; Kobayakawa, Y. Org. Lett. 2011,
13, 6268–6271; (b) Cristau, P. Tetrahedron 2003, 59, 7859–7870.
5. (a) Ullmann, F. Ber. Dtsch. Chem. Ges. 1904, 37, 853–854; (b) Goldberg, I. Ber.
Dtsch. Chem. Ges. 1906, 39, 1691–1692.
6. For C–O, please see: (a) Burgos, C. H.; Barder, T. E.; Huang, X.; Buchwald, S. L.
Angew. Chem., Int. Ed. 2006, 45, 4321–4326; (b) Mann, G.; Incarvito, C.;
Rheingold, A. L.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 3224–3225; (c) Hu, T.;
Schulz, T.; Torborg, C.; Chen, X.; Wang, J.; Beller, M.; Huang, J. Chem. Commun.
2009, 7330–7332; (d) Salvi, L.; Davis, N. R.; Ali, S. Z.; Buchwald, S. L. Org. Lett.
2011, 14, 170–173; (e) Harkal, S.; Kumar, K.; Michalik, D.; Zapf, A.; Jackstell, R.;
Rataboul, F.; Riermeier, T.; Monsees, A.; Beller, M. Tetrahedron Lett. 2005, 46,
3237–3240. For selective C–N, please see:; (f) Shen, Q.; Ogata, T.; Hartwig, J. F. J.
17. Yoshida, H.; Sugiura, S.; Kunai, A. Org. Lett. 2002, 4, 2767–2769.