Mild Conditions for Copper-Catalyzed
N-Arylation of Imidazoles

Huaming Chen; Deping Wang; Xianyang Wang; Wenlong Huang; Qian Cai; Ke Ding

doi:10.1055/s-0029-1218691

PAPER

Mild Conditions for Copper-Catalyzed N-Arylation of Imidazoles

Huaming Chen^a, Deping Wang^b,c, Xianyang Wang^d, Wenlong Huang*^a, Qian Cai^b, Ke Ding*^b
^a China Pharmaceutical University, # 24 Tongjiaxiang, Nanjing 210009, P. R. of China
e-Mail: ydhuangwenlong@126.com;
^b Key Laboratory of Regenerative Biology and Institute of Chemical Biology, Guangzhou Institutes of Biomedicine and Health, Chinese Academy of Sciences, Guangzhou International Business Incubator D-10, Guangzhou Science Park, Guangzhou 510663, P. R. of China
Fax: +86(20)32290606.; e-Mail: ding_ke@gibh.ac.cn;
^c Graduate School of the Chinese Academy of Sciences, Chinese Academy of Sciences, 19AYuquan Road, Beijing 100049, P. R. of China
^d Jiangsu Provincial Institute of Materia Medica, Nanjing University of Technology, 5 Xinmofan Road, Nanjing 210009, P. R. of China

Abstract

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Abstract

An efficient copper(I) bromide catalyzed N-arylation of azoles with a variety of aromatic bromides and iodides under mild conditions is reported. This reaction displayed great functional group compatibility and excellent reactive selectivity.

Key words

copper - aryl halides - imidazoles - azoles - N-arylation

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Referenzen

References

For recent reviews, see:

1a Wiglenda T. Ott I. Kircher B. Schumacher P. Schuster D. Langer T. Gust R. J. Med. Chem. 2005, 48: 6516

1b Jin Z. Nat. Prod. Rep. 2005, 22: 196

1c De Luca L. Curr. Med. Chem. 2006, 13: 1

1d Campeau L.-C. Fagnou K. Chem. Soc. Rev. 2007, 1058

1e Wiglenda T. Gust R. J. Med. Chem. 2007, 50: 1475

1f Kison C. Opatz T. Chem. Eur. J. 2009, 15: 843

2a Herrmann WA. Angew. Chem. Int. Ed. 2002, 41: 1290

2b Vargas VC. Rubio RJ. Hollis TK. Salcido ME. Org. Lett. 2003, 5: 4847

2c Perry MC. Cui X. Powell MT. Hou D.-R. Reibenspies JH. Burgess K. J. Am. Chem. Soc. 2003, 125: 113

2d Nair V. Bindu S. Sreekumar V. Angew. Chem. Int. Ed. 2004, 43: 5130

2e Enders D. Niemeier O. Henseler A. Chem. Rev. 2007, 107: 5606

Recent reviews on copper-catalyzed Ullmann reactions see:

3a Hassan J. Sevignon M. Gozzi C. Schulz E. Lemaire M. Chem. Rev. 2002, 102: 1359

3b Kunz K. Scholz U. Ganzer D. Synlett 2003, 2428

3c Ley SV. Thomas AW. Angew. Chem. Int. Ed. 2003, 42: 5400

3d Beletskaya IP. Cheprakov AV. Coord. Chem. Rev. 2004, 248: 2337

3e Monnier F. Taillefer M. Angew. Chem. Int. Ed. 2008, 47: 3096

3f Evano G. Blanchard N. Toumi M. Chem. Rev. 2008, 108: 3054

3g Ma D. Cai Q. Acc. Chem. Res. 2008, 41: 1450

3h Monnier F. Taillefer M. Angew. Chem. Int. Ed. 2009, 48: 6954

4 Lindley J. Tetrahedron 1984, 40: 1433

5a Klapars A. Antilla JC. Huang X. Buchwald SL. J. Am. Chem. Soc. 2001, 123: 7727

5b Antilla JC. Klapars A. Buchwald SL. J. Am. Chem. Soc. 2002, 124: 11684

5c Antilla JC. Baskin JM. Barder TE. Buchwald SL. J. Org. Chem. 2004, 69: 5578

5d Altman RA. Buchwald SL. Org. Lett. 2006, 8: 2779

5e Altman RA. Koval ED. Buchwald SL. J. Org. Chem. 2007, 72: 6190

5f Jiang Q. Jiang D. Jiang Y. Fu H. Zhao Y. Synlett 2007, 1836

5g de Lange B. Lambers-Verstappen MH. de Vondervoort LS. Sereinig N. de Rijk R. de Vries AHM. de Vries JG. Synlett 2006, 3105

5h Cristau HJ. Cellier PP. Spindler JF. Taillefer M. Chem. Eur. J. 2004, 10: 5607

5i Zhang H. Cai Q. Ma D. J. Org. Chem. 2005, 70: 5164

5j Jerphagnon T. van Klink GPM. de Vries JG. van Koten G. Org. Lett. 2005, 7: 5241

5k Xie Y.-X. Pi S.-F. Wang J. Yin D.-L. Li J.-H. J. Org. Chem. 2006, 71: 8324

5l Liu L. Frohn M. Xi N. Dominguez C. Hungate R. Reider PJ. J. Org. Chem. 2005, 70: 10135

5m Zhu L. Cheng L. Zhang Y. Xie R. You J. J. Org. Chem. 2007, 72: 2737

5n Lv X. Bao W. J. Org. Chem. 2007, 72: 3863

5o Guo X. Rao H. Fu H. Jiang Y. Zhao Y. Adv. Synth. Catal. 2007, 348: 2197

5p Ma H. Jiang X. J. Org. Chem. 2007, 72: 8943

5q Cheng D. Gan F. Qian W. Bao W. Green Chem. 2008, 10: 171

5r Suresh P. Pitchumani K. J. Org. Chem. 2008, 73: 9121

5s Liang L. Li Z. Zhou X. Org. Lett. 2009, 11: 3294

5t Wang Y. Wu Z. Wang L. Li Z. Zhou X. Chem. Eur. J. 2009, 15: 8971

5u Xi Z. Liu F. Zhou Y. Chen W. Tetrahedron 2008, 64: 4254

5v Taillefer M. Xia N. Ouali A. Angew. Chem. Int. Ed. 2007, 46: 934

5w Bolm C. Correa A. Adv. Synth. Catal. 2007, 349: 2673

5x Wan J. Chai Y. Wu J. Pan Y. Synlett 2008, 3068

5y Bao W. Liu Y. Lv X. Synthesis 2008, 1911

5z Cheng C. Sun G. Wan J. Sun C. Synlett 2009, 2663

6 Zhu L. Li G. Luo L. Guo P. Lan J. You J. J. Org. Chem. 2009, 74: 2200

7a Wang D. Ding K. Chem. Commun. 2009, 1891

7b Wang D. Cai Q. Ding K. Adv. Synth. Catal. 2009, 351: 1722

7c Zhang Q. Wang D. Wang X. Ding K. J. Org. Chem. 2009, 74: 7187

8a Huang W. Shakespeare W. C. Synthesis 2007, 2121

8b Khan M. A. Polya J. B. Rev. Latinoam. Quim. 1972, 3: 119