Bifunctional Salen-Cu(II) complex as efficient catalyst for N-arylation of imidazoles and Suzuki-Miyaura coupling reactions

Abstract

Bifunctional Salen-Cu(II) complex catalyzed cross-coupling reactions of aryl halids with imidazoles or phenylboronic acid reagents have been developed as practical methods for C―N and C―C bond formation. The procedure tolerates aryl halides with various functional groups(such as methoxy, acetyl, nitrile, fluoro and nitro groups) and gives the corresponding coupling products in moderate to high yields. The catalyst remained active after five successive catalytic runs without loss in performance.

Keywords

Salen-Cu(II) complex / Homogenous catalysis / Cross-coupling / N-arylation

References

[1] Thomas K. R. J., Lin J. T., Tao Y. T., Ko C. W., J A.m. Chem. Soc, 2001, 123(123): 9404.

[2] Ley S. V., Thomas A. W. Angew. Chem. Int. Ed, 2003, 42(42): 5400.

[3] Kinzel T., Zhang Y., Buchwald S. L., J A.m. Chem. Soc, 2010, 132(132): 1407.

[4] Ghosh R., Adarsh N. N., Sarkar A. J. Org. Chem, 2010, 75(75): 5320.

[5] Fliedel C., Braunstein P. Organometallics, 2010, 29(29): 5614.

[6] Huynh H. V., Yeo C. H., Chew Y. X. Organometallics, 2010, 29(29): 1479.

[7] Karimi B., Akhavan P. F., Chem. Commun., 2009, (25), 3750.

[8] Alonso D. A., Nájera C., Pacheco M. C. J. Org. Chem, 2002, 67(67): 5588.

[9] Alonso D. A., Nájera C., Pacheco M. C. Org. Lett, 2000, 2(2): 1823.

[10] Zhou J., Li X., Sun H. J. Organometal. Chem, 2010, 695(695): 297.

[11] Chen C. L., Liu Y. H., Peng S. M., Liu S. T. Organometallics, 2005, 24(24): 1075.

[12] Cui J., Zhang M., Zhang Y. Inorg. Chem. Commun, 2010, 13: 81.

[13] Schnyder A., Indolese A. F., Studer M., Blaser H. U. Angew. Chem. Int. Ed, 2002, 41(41): 3668.

[14] Dai M., Liang B., Wang C., Chen J., Yang Z. Org. Lett., 2004, 6(6): 221.

[15] Ma D., Cai Q. Acc. Chem. Res, 2008, 41(41): 1450.

[16] Siddle J. S., Batsanov A. S., Bryce M. R., Eur J. Org. Chem, 2008, 16: 2746.

[17] Wu M., Mao J., Gou J., Ji S., Eur J. Org. Chem, 2008, 23: 4050.

[18] Suresh P., Pitchuman K. J. Org. Chem, 2008, 73(73): 9121.

[19] Jammi S., Sakthivel S., Rout L., Mukherjee T., Mandai S., Mitra R., Saha P., Punniyamurthy T. J. Org. Chem, 2009, 74: 1971.

[20] Strieter E. R., Bhayana B., Buchwald S. L., J A.m. Chem. Soc, 2009, 131(131): 12898.

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

[22] Cristau H. J., Cellier P. P. S., indler J F., Taillefer M. Chem. Eur. J, 2004, 10(10): 5607.

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

[24] Khare S., Chokhare R. J. Mol. Cat. A: Chem, 2012, 353: 138.

[25] Chai L. Q., Wang G., Sun Y. X., Dong W. K., Zhao L., Gao X. H. J. Coord. Chem, 2012, 65: 1621.

[26] Zeynep T., Mahmut U. J. Organometal. Chem, 2012, 713: 104.

[27] Olav S., Guido C. H., Thomas C., Stephan R. Angew. Chem. Int. Ed, 2010, 49(49): 4927.

[28] Minutolot F., Pinit D., Petri A., Salvadort P. Tetrahedron: Asymmetry, 1996, 7(7): 2293.

[29] Bahramian B., Mirkhani V., Moghadam M., Tangestaninejad S. Cat. Commun, 2006, 7: 289.

[30] Campeau L. C., Fagnou K. Chem. Soc. Rev, 2007, 36(36): 1058.

[31] Wiglenda T., Gust R. J. Med. Chem, 2007, 50(50): 1475.

[32] Kison C., Opatz T. Chem. Eur. J, 2009, 15(15): 843.

[33] Wang Z., Skerlj R. T., Bridger G. J. Tetrahedron Lett, 1999, 40(40): 3543.

[34] Mann G., Hartwig J. F. Tetrahedron Lett, 1997, 38(38): 8005.

[35] Wolter M., Nordmann G., Job G. E., Buchwald S. L. Org. Lett, 2002, 4(4): 973.

[36] Nordmann G., Buchwald S. L., J A.m. Chem. Soc, 2003, 125(125): 4978.