1,1′-binaphthyl-2,2′-diamine dihydrochloride: an efficient ligand for the N-arylation of imidazole with aryl/heteroaryl halides catalyzed by CuI

Abstract

Employing 1,1′-binaphthyl-2,2′-diamine(BINAM) dihydrochloride as an efficient and commercially available ligand, relatively mild and highly efficient copper-catalyzed coupling reactions of imidazole with aryl and heteroaryl halides have been developed. Various N-arylimidazoles could be synthesized in moderate to excellent yields.

Keywords

Copper-catalyzed N-arylation / N-Arylimidazole / Ullmann-type coupling

References

[1] Porres L., Mongin O., Katan C., Charlot M., Pons T., Mertz J., Blan-chard-Desce M. Org. Lett., 2004, 6: 47.

[2] Kison C., Opatz T. Chem.-Eur. J., 2009, 15: 843.

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

[4] Monnier F., Taillefer M. Angew. Chem. Int. Ed., 2008, 47: 3096.

[5] Liang L., Li Z., Zhou X. Org. Lett., 2009, 15: 3294.

[6] Engel-Andreasen J., Shimpukade B., Ulven T. Green Chem., 2013, 15: 336.

[7] Ji W., Qu J., Jing S., Zhu D., Huang W. Dalton Trans., 2016, 45: 1016.

[8] Ullmann F., Wenner P. Ber. Dtsch. Chem. Ges., 1903, 327: 120.

[9] Ullmann F., Meyer G., Loewenthal O. Ber. Dtsch. Chem. Ges., 1904, 332: 38.

[10] Corbert J. P., Mignani G. Chem. Rev., 2006, 106: 2651.

[11] Prim D., Campagne J. M., Joseph D., Andrioletti B. Tetrahedron, 2002, 58: 2041.

[12] Beare N. A., Hartwig J. F. J. Org. Chem., 2002, 67: 541.

[13] Kataoka K. N., Shelby Q., Stambuli J. P., Hartwig J. F. J. Org. Chem., 2002, 67: 5553.

[14] Yin J., Buchwald S. L. J. Am. Chem. Soc., 2002, 124: 6043.

[15] Grasa G. A., Viciu M. S., Huang J., Nolan S. P. J. Org. Chem., 2001, 66: 7729.

[16] Arterburn J. B., Pannala M., Gonzalez A. M. Tetrahedron Lett., 2001, 42: 1475.

[17] Cristau H. J., Vogel R., Taillefer M. A. Tetrahedron Lett., 2000, 41: 8457.

[18] Tasler S., Lipshutz B. H. J. Org. Chem., 2003, 68: 1190.

[19] Kwong F. Y., Klapars A., Buchwald S. L. Org. Lett., 2002, 4: 581.

[20] Kwong F. Y., Buchwald S. L. Org. Lett., 2003, 5: 793.

[21] Ma D., Zhang Y., Yao J., Wu S., Tao F. J. Am. Chem. Soc., 1998, 120: 12459.

[22] Ma D., Xia C. Org. Lett., 2001, 3: 2583.

[23] Ma D., Cai Q., Zhang H. Org. Lett., 2003, 5: 2453.

[24] Ma D., Cai Q. Org. Lett., 2003, 5: 3799.

[25] Cristau H. J., Cellier P. P., Spindler J. F., Taillefer M. Eur. J. Org. Chem., 2004, 695.

[26] Cristau H. J., Cellier P. P., Spindler J. F., Taillefer M. Chem. Eur. J., 2004, 10: 5607.

[27] Wang Y., Gao J., Zhao M., Li J. Chem. Res. Chinese Universities, 2015, 31(4): 549.

[28] Kelkar A. A., Patil N. M., Chaudhari R. V. Tetrahedron Lett., 2002, 43: 7143.

[29] Gajare A. S., Toyota K., Oshifuji M., Ozawab Y. F. Chem. Commun., 2004, 1994.

[30] Rao H., Fu H., Jiang Y., Zhao Y. J. Org. Chem., 2005, 70: 8107.

[31] Cheng D. P., Gan F. F., Qian W. X., Bao W. L. Green Chem., 2008, 10: 171.

[32] Engel-Andreasen J., Shimpukade B., Ulven T. Green Chem., 2013, 15: 336.

[33] Singh R., Allam B. K., Raghuvanshi D. S., Singh K. N. Tetrahedron, 2013, 69: 1038.

[34] Nemeth J., Debreczeni N., Gresits I., Maria B., Zoltan H. Catal Lett., 2015, 145: 1113.

[35] Hosseini-Sarvari M., Moeini F. RSC Adv., 2014, 4: 7321.

[36] Güell I., Ribas X. Eur. J. Org. Chem., 2014, 3188.

[37] Ziegler D. T., Choi J., Munoz-Molina J. M., Bissember A. C., Peters J. C., Fu G. C. J. Am. Chem. Soc., 2013, 135: 13107.

[38] Wu F. T., Liu P., Ma X. W., Xie J. W., Dai B. Chin. Chem. Lett., 2013, 24: 893.

[39] Antilla J. C., Klapars A., Buchwald S. L. J. Am. Chem. Soc., 2002, 124: 11684.

[40] Allen D. V., Venkataraman D. J. Org. Chem., 2003, 68: 4590.

[41] Zhu R., Xing L. X., Wang X. Y., Cheng C. J., Su D. Y., Hu Y. F. Adv. Synth. Catal., 2008, 350: 1253.

[42] Correa A., Bolm C. Adv. Synth. Catal., 2007, 349: 2673.

[43] Sperotto E., de Vries J. G., van Klink G. P. M., van Koten G. Tetra-hedron Lett., 2007, 48: 7366.

[44] Liu Y. S., Gu N. N., Liu P., Xie J. W., Dai B., Liu Y. Appl. Organo-metal. Chem., 2015, 29: 468.

[45] Naidu A. B., Raghunath O. R., Prasad D. J. C., Sekar G. Tetrahedron Lett., 2008, 49: 1057.

[46] Naidu A. B., Sekar G. Tetrahedron Lett., 2008, 49: 3147.

[47] Altman R. A., Buchwald S. L. Org. Lett., 2006, 8: 2779.

[48] Yang K., Qiu Y., Li Z., Wang Z., Jiang S. J. Org. Chem., 2011, 76: 3151.

[49] Lv X., Wang Z., Bao W. L. Terahedron, 2006, 62: 4756.

[50] Glushkov V. A., Valieva M. S., Maiorova O. A., Baigacheva E. V., Gorbunov A. A. Rusian J. Org. Chem., 2011, 47: 230.