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http://dx.doi.org/10.5012/bkcs.2014.35.10.3009

C-H Arylation of Nitroimidazoles and Nitropyrazoles Guided by the Electronic Effect of the Nitro Group  

Jung, Haeun (Department of Chemistry, Pusan National University)
Bae, Seri (Department of Chemistry, Pusan National University)
Jang, Ha-Lim (Department of Chemistry, Pusan National University)
Joo, Jung Min (Department of Chemistry, Pusan National University)
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Abstract
A palladium-catalyzed C-H arylation reaction of nitroimidazoles and nitropyrazoles was developed using aryl bromides as arene donors. The electron-withdrawing effect of the nitro group allows for direct C-H arylation reactions of the nitro diazoles with high regioselectivity under mild conditions. The new C-H arylation approach is thus complementary to nucleophilic substitution reactions, enabling the preparation of complex nitroazole compounds.
Keywords
C-H arylation; Nitroimidazole; Nitropyrazole; Palladium;
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1 (c) Yan, T.; Chen, L.; Bruneau, C.; Dixneuf, P. H.; Doucet, H. J. Org. Chem. 2012, 77, 7659.   DOI   ScienceOn
2 Caron, L.; Campeau, L.-C.; Fagnou, K. Org. Lett. 2008, 10, 4533.   DOI   ScienceOn
3 Guo, P.; Joo, J. M.; Rakshit, S.; Sames, D. J. Am. Chem. Soc. 2011, 133, 16338.   DOI   ScienceOn
4 (a) Kakiuchi, F.; Chatani, N. Adv. Synth. Catal. 2003, 345, 1077.   DOI   ScienceOn
5 (a) Goikhman, R.; Jacques, T. L.; Sames, D. J. Am. Chem. Soc. 2009, 131, 3042.   DOI   ScienceOn
6 (b) Joo, J. M.; Toure, B. B.; Sames, D. J. Org. Chem. 2010, 75, 4911.   DOI   ScienceOn
7 Review: Mąkosza, M.; Wojciechowski, K. Chem. Rev. 2004, 104, 2631.   DOI
8 (b) Alberico, D.; Scott, M. E.; Lautens, M. Chem. Rev. 2007, 107, 174.   DOI   ScienceOn
9 (c) Satoh, T.; Miura, M. Chem. Lett. 2007, 36, 200.   DOI   ScienceOn
10 (d) Seregin, I. V.; Gevorgyan, V. Chem. Soc. Rev. 2007, 36, 1173.   DOI   ScienceOn
11 (e) Chen, X.; Engle, K. M.; Wang, D.-H.; Yu, J.-Q. Angew. Chem., Int. Ed. 2009, 48, 5094.   DOI   ScienceOn
12 (f) Colby, D. A.; Bergman, R. G.; Ellman, J. A. Chem. Rev. 2010, 110, 624.   DOI   ScienceOn
13 (g) Lyons, T. W.; Sanford, M. S. Chem. Rev. 2010, 110, 1147.   DOI   ScienceOn
14 (h) Yamaguchi, J.; Yamaguchi, A. D.; Itami, K. Angew. Chem. Int. Ed. 2012, 51, 8960.   DOI   ScienceOn
15 Crozet, M. D.; Suspene, C.; Kaafarani, M.; Crozet, M. P.; Vanelle, P. Heterocycles 2004, 63, 1629.   DOI
16 Crozet, M. D.; Zink, L.; Remusat, V.; Curti, C.; Vanelle, P. Synthesis 2009, 18, 3150.
17 (a)Bellina, F.; Rossi, R. Tetrahedron 2009, 65, 10269.   DOI   ScienceOn
18 (b) Ackermann, L. Chem. Rev. 2011, 111, 1315.   DOI   ScienceOn
19 Prat, D.; Pardigon, O.; Flemming, H.-W.; Letestu, S.; Ducandas, V.; Isnard, P.; Guntrum, E.; Senac, T.; Ruisseau, S.; Paul Cruciani, P.; Hosek, P. Org. Process Res. Dev. 2013, 17, 1517.   DOI   ScienceOn
20 Tobisu, M.; Hyodo, I.; Chatani, N. J. Am. Chem. Soc. 2009, 131, 12070.   DOI   ScienceOn
21 Joo, J. M.; Guo, P.; Sames, D. J. Org. Chem. 2013, 78, 738.   DOI   ScienceOn
22 Shibahara, F.; Yamaguchi, E.; Murai, T. J. Org. Chem. 2011, 76, 2680.   DOI   ScienceOn
23 Chiong, H. A.; Daugulis, O. Org. Lett. 2007, 9, 1449.   DOI   ScienceOn
24 Denmark, S. E.; Schnute, M. E. J. Org. Chem. 1995, 60, 1013.   DOI   ScienceOn
25 (c) Crozet, M. D.; Botta, C.; Gasquet, M.; Curti, C.; Remusat, V.; Hutter, S.;Chapelle, O.; Azas, N.; De Méo, M.; Vanelle, P. Eur. J. Med.Chem. 2009, 44, 653.   DOI   ScienceOn
26 (b) Duan, Y.-T.; Wang, Z.-C.; Sang, Y.-L.; Tao, X.-X.; Teraiya, S. B.; Wang, P.-F.; Wen, Q.; Zhou, X.-J.; Ding, L.; Yang, Y.-H.; Zhu, H.-L. Eur. J. Med. Chem. 2014, 76, 387.   DOI   ScienceOn
27 Lyudmila, L.; Valentin, L. Nitroazoles: Synthesis, Structure and Applications; Springer: New York, 2009.
28 (a) Rami, M.; Dubois, L.; Parvathaneni, N.-K.; Alterio, V.; van Kuijk, S. J. A.; Monti, S. M.; Lambin, P.; De Simone, P.; Supuran, C. T.; Winum, J.-Y. J. Med. Chem. 2013, 56, 8512.   DOI   ScienceOn
29 (a) Smitrovich, J. H.; Davies, I. W. Org. Lett. 2004, 6, 533.   DOI   ScienceOn
30 (a) The Nitro Group in Organic Synthesis; Ono, N., Ed.; Wiley-VCH: New York, 2001.
31 (b) Freeman, A. W.; Urvoy, M.; Criswell, M. E. J. Org. Chem. 2005, 70, 5014.   DOI   ScienceOn
32 (c) Sanz, R.; Escribano, J.; Pedrosa, M. R.; Aguado, R.; Arnaiz, F. J. Adv. Synth. Catal. 2007, 349, 713.   DOI   ScienceOn
33 (a) Liegault, B.; Petrov, I.; Gorelsky, S. I.; Fagnou, K. J. Org. Chem. 2010, 75, 1047.   DOI   ScienceOn
34 (b) Mateos, C.; Mendiola, J.; Carpintero, M.; Mínguez, J. M. Org. Lett. 2010, 12, 4924.   DOI   ScienceOn
35 Iaroshenko, V. O.; Gevorgyan, A.; Davydova, O.; Villinger, A.; Langer, P. J. Org. Chem. 2014, 79, 2906.   DOI   ScienceOn
36 (b) Hanan, E. J.; van Abbema, A.; Barrett, K.; Blair, W. S.; Blaney, J.; Chang, C.; Eigenbrot, C.; Flynn, S.; Gibbons, P.; Hurley, C. A.; Kenny, J. R., II.; Kulagowski, J.; Lee, L.; Magnuson, S. R.; Morris, C.; Murray, J.; Pastor, R. M.; Rawson, T.; Siu, M.; Ultsch, M.; Zhou, A.; Sampath, D.; Lyssikatos, J. P. J. Med. Chem. 2012, 55, 10090.   DOI   ScienceOn