Researches on the Hydrodehalogenation of o-Triazole Aryl Halides in the System of Pd/C and Et3N

  • Qiu Huihua ,
  • Lin Baiyin ,
  • Zhou Peng ,
  • Zhang Jiantao ,
  • Liu Weibing
Expand
  • College of Chemistry, Guangdong University of Petrochemical Technology, Maoming, Guangdong 525000

Received date: 2019-12-08

  Revised date: 2020-01-04

  Online published: 2020-01-15

Supported by

Project supported by the National Natural Science Foundation of China (No. 21602035), the Natural Science Foundation of Guangdong Province (No. 2016A030307030) and the Program for Innovative Research Team of Guangdong University of Petrochemical Technology (No. 519124).

Abstract

The hydrodehalogenation of halogenated organic compounds which have brought serious pollution to the environment can not only transform them into other usefull chemicals, but also reduce their pollution in the field of environment. A Pd-catalyzed hydrodehalogenation of o-triazole aryl halides is introduced, taking Pd/C as catalyst and Et3N as base, reductant and hydrogen source. This strategy is highlighted by appealing features such as simple reaction condition, recyclable catalyst, and good yield etc.

Cite this article

Qiu Huihua , Lin Baiyin , Zhou Peng , Zhang Jiantao , Liu Weibing . Researches on the Hydrodehalogenation of o-Triazole Aryl Halides in the System of Pd/C and Et3N[J]. Chinese Journal of Organic Chemistry, 2020 , 40(5) : 1372 -1377 . DOI: 10.6023/cjoc201912010

References

[1] (a) Mitoma, Y.; Nagashima, S.; Simion C.; Simion A. M.; Yamada, T.; Mimura K.; Ishimoto, K.; Tashiro, M. Environ. Sci. Technol. 2001, 35, 4145.
(b) Mitoma, Y.; Uda, T.; Egashira, N.; Simion, C.; Tashiro, H.; Tashiro, M.; Fan, X. Environ. Sci. Technol. 2004, 38, 1216.
(c) Mitoma, Y.; Tasaka, M.; Takase, M.; Masuda, T.; Tashiro, H.; Egashira, N.; Oki, T. Environ. Sci. Technol. 2006, 40, 1849.
(d) Mitoma, Y.; Kakeda, M.; Simion, A. M.; Egashira, N.; Simion, C. Environ. Sci. Technol. 2009, 43, 15, 5952.
[2] Alonso, F.; Beletskaya, I. P.; Yus M. Chem. Rev. 2002, 102, 4009.
[3] (a) Guram, A. S.; Rennels, R. A.; Buchwald, S. L. Angew. Chem., Int. Ed. Engl. 1995, 34, 1348.
(b) Marcoux, J.-F.; Wagaw, S.; Buchwald, S. L. J. Org. Chem. 1997, 62, 1568.
(c) Wolfe, J. P.; Buchwald, S. L. J. Org. Chem. 2000, 65, 1144.
[4] (a) Jones, J. R.; William, J. S.; Lockley, S. L.; Stewart, P. Tetrahedron Lett. 2001, 42, 331.
(b) Uozumi, Y.; Nakao, R.; Rhee, H. Org. Lett. 2005, 7, 163.
[5] (a) Rodriguez, J. G.; Lafuente, A. Tetrahedron Lett. 2002, 43, 9645.
(b) Cellier, P. P.; Spindler, J. F.; Taillefera, M.; Cristaua, H. J. Tetrahedron Lett. 2003, 44, 7191.
[6] Zawisza, A. M.; Muzart, J. Tetrahedron Lett. 2007, 48, 6748. (DMF)
[7] (a) Viciu, M. S.; Grasa, G. A.; Nolan, S. P. Organometallics 2001, 20, 3607.
(b) Navarro, O.; Kaur, H.; Nolan, S. P. J. Org. Chem. 2004, 69, 3173.
[8] Pyo, A.; Kin, S.; Kumar, M. R.; Byeun, A.; Eom, M. S.; Han, M. S.; Lee, S. Tetrahedron Lett. 2013, 54, 5207.
[9] Yamamoto, Y.; Nogi, K.; Yorimitsu, H.; Osuka, A. ChemistrySelect 2017, 2, 1723.
[10] Bhattacharjya, A.; Klumphu, P.; Lipshutz, B. H. Org. Lett. 2015, 17, 1122.
[11] Qiu, H.; Zhou, P.; Liu, W.; Zhang, J.; Chen, B. ChemistrySelect 2020, 5, 2935.
[12] (a) Zou, B.; Jiang, H.; Wang, Z. Eur. J. Org. Chem. 2007, 4600.
(b) Zou, B.; Jiang, H. Chin. J. Chem. 2008, 26, 1309.
(c) Roy, S. K.; Tiwari, A.; Saleem, M.; Jana, C. K. Chem. Commun. 2018, 54, 14081.
(d) Zhang, D.; Khan, R.; Yang, F.; Zhang, X.; Shen, G.; Gao, Y.; Fan, R.; Sun, W.; Fan, B. Eur. J. Org. Chem. 2018, 3464.
[13] Zhang, Z.; Song, P.; Zhou, J.; Chen, Y.; Lin, B.; Li, Y. Ind. Eng. Chem. Res. 2016, 55, 12301.
[14] Özçubukçu, S.; Ozkal, E.; Jimeno, C.; Pericàs, M. A. Org. Lett. 2009, 11, 4680.
[15] Asano, K.; Matsubara, S. Org. Lett. 2010, 12, 4988.
[16] Shin, J.; Lim, Y.; Lee, K. J. Org. Chem. 2012, 77, 4117.
[17] Adenot, A.; Landstrom, E. B.; Gallou, F.; Lipshutz, B. H. Green Chem. 2017, 19, 2506.
[18] Ötvös, S. B.; Hatoss, G.; Georgiádes, Á.; Kovács, S.; Mándity, I. M.; Novák, Z.; Fülöp, F. RSC Adv. 2014, 4, 46666.
[19] Chen, Z.; Yan, Q.; Yi, H.; Liu, Z.; Lei, A.; Zhang, Y. Chem.-Eur. J. 2014, 20, 13692.
[20] Asano, K.; Matsubara, S. Org. Lett. 2010, 12, 4988.
[21] Park, I. S.; Kwon, M. S.; Kim, Y.; Lee, J. S.; Park, J. Org. Lett. 2008, 10, 497.
[22] Yamada, Y.M.A.; Ohno, A.; Sato, T.; Uozumi, Y. Chem.-Eur. J. 2015, 21, 17269.
[23] Ramachary, D.B., Shashank, A.B. and Karthik, S. Angew. Chem., Int. Ed. 2014, 53, 10420.
[24] Kafle, A.; Handy, S. T. Tetrahedron 2017, 73, 7024.
Outlines

/