Facile Synthesis of 1,5-Diaryl-4-pyridyl-1,2,3-triaozle Derivatives

Abstract

A feasible approach to synthesize 1,5-diaryl-4-pyridyl-1,2,3-triaozle via a sequential route from 2-alkynyl pyridine was developed. In this work, KOH was identified as a crucial base to promote the Pd-catalyzed arylation step. Compared to the reported methods, this protocol largely improved the reaction efficiency with overall excellent yield and good functional group tolerance.

Keywords

1,2,3-Triazole / Arylation / Triazole ligand

References

[1] Aromi G., Barrios L. A., Roubeau O., Gamez P. C. oord. Chem. Rev., 2011, 255: 485.

[2] Hein J. E., Fokin V. V. Chem. Soc. Rev., 2010, 39: 1302.

[3] Huang D. S., Zhao P. X., Astruc D. Coord. Chem. Rev., 2014, 272: 145.

[4] Monguchi Y., Sawama Y., Sajiki H. Heterocycles, 2015, 91: 239.

[5] Verma A. K., Jha R. R., Chaudhary R., Tiwari R. K., Danodia A. K. Adv. Synth. Catal., 2013, 355: 421.

[6] Liu Z. H., Wang Y. N., Sun J. B., Yang Y., Liu Q. W., Song Z. G. C. hem. Res. Chinese Universities, 2015, 31(4): 526.

[7] Duan H., Sengupta S., Petersen J. L., Akhmedov N. G., Shi X. J. Am. Chem. Soc., 2009, 131: 12100.

[8] Saravanakumar R., Ramkumar V., Sankararaman S. O. rganometallics, 2011, 30: 1689.

[9] Wang K., Chen M., Wang Q., Shi X., Lee J. K. J. Org. Chem., 2013, 78: 7249.

[10] Albrecht M., Koten G. Angew. Chem. Int. Ed., 2001, 40: 3750.

[11] Gunanathan C., Milstein D. Acc. Chem. Res., 2011, 44: 588.

[12] Gunanathan C., Milstein D. Chem. Rev., 2014, 114: 12024.

[13] Leis W., Mayer H. A., Kaska W. C. C. oord. Chem. Rev., 2008, 252: 1787.

[14] Milstein D. Top. Catal., 2010, 53: 915.

[15] Pandarus V., Zargarian D. Organometallics, 2007, 26: 4321.

[16] Schneider S., Meiners J., Askevold B. Eur. J. Inorg. Chem., 2012, 2012: 412.

[17] Selander N., Szabo K. J. Chem. Rev., 2011, 111: 2048.

[18] Zell T., MIlstein D. Acc. Chem. Res., 2015, 48: 1979.

[19] Fletcher J. T., Bumgarner B. J., Engels N. D., Skoglund D. A. Organometallics, 2008, 27: 5430.

[20] Li Y., Zhao L., Tam A. Y. Y., Wong K. M. C., Wu L., Yam V. W. W. Chem. Eur. J., 2013, 19: 14496.

[21] Allampally N. K., Daniliuc C. G., Strassert C. A., Cola L. D. Inorg. Chem., 2015, 54: 1588.

[22] Chan A. K. W., Wu D., Wong K. M. C., Yam V. W. W. Inorg. Chem., 2016, 55: 3685.

[23] Meudtner R. M., Ostermeier M., Goddard R., Limberg C., Hecht S. Chem. Eur. J., 2007, 13: 9834.

[24] Chuprakov S., Chernyak N., Dudnik A. S., Gevorgyan V. O. rg. Lett., 2007, 9: 2333.

[25] Ackermann L., Vicente R., Born R. Adv. Synth. Catal., 2008, 35: 741.

[26] Ackermann L., Potukuchi H. K., Landsberg D., Vicente R. Org. Lett., 2008, 10: 3081.