Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
RESEARCH ARTICLE

High Catalytic Activity of Peptide Nanofibres Decorated with Ni and Cu Nanoparticles for the Synthesis of 5-Substituted 1H-Tetrazoles and N-Arylation of Amines

Arash Ghorbani-Choghamarani A B and Zahra Taherinia A
+ Author Affiliations
- Author Affiliations

A Department of Chemistry, Ilam University, PO Box 69315516, Ilam, Iran.

B Corresponding author. Email: a.ghorbani@ilam.ac.ir

Australian Journal of Chemistry - https://doi.org/10.1071/CH17176
Submitted: 30 March 2017  Accepted: 29 May 2017   Published online: 11 July 2017

Abstract

A rapid development of a new methodology for decarboxylative N-arylation of carboxylic acids and the preparation of 5-substituted 1H-tetrazoles catalysed by peptide nanofibres decorated with Cu and Ni nanoparticles is presented. Compared with conventional aryl halides, benzoic acids are extremely interesting and environmentally friendly options for the synthesis of secondary aryl amines.


References

[1]  J. Safaei-Ghomi, Z. Akbarzadeh, B. Khojastehbakht-Koopaei, RSC Adv. 2015, 5, 28879.
         | CrossRef | 1:CAS:528:DC%2BC2MXksV2ksL4%3D&md5=15583c2f4cc39a630cb9b11f4fbc0169CAS | open url image1

[2]  K. Karami, N. Haghighat Naeini, Turk. J. Chem. 2015, 39, 1199.
         | CrossRef | 1:CAS:528:DC%2BC28XisVKnt7k%3D&md5=cd6b93913e330fa6707badef32b0c25aCAS | open url image1

[3]  P. Ruiz-Castillo, S. L. Buchwald, Chem. Rev. 2016, 116, 12564.
         | CrossRef | 1:CAS:528:DC%2BC28XhsFymu7bJ&md5=37db2c7465adbc2fc973bf8786726717CAS | open url image1

[4]  N. Barot, S. B. Patel, H. Kaur, J. Mol. Catal. Chem. 2016, 423, 77.
         | CrossRef | 1:CAS:528:DC%2BC28XhtVKnsrnF&md5=682a19cfe1af1adb2a384489e83f2c40CAS | open url image1

[5]  M. Mondal, S. K. Bharadwaj, U. Bora, New J. Chem. 2015, 39, 31.
         | CrossRef | 1:CAS:528:DC%2BC2cXhsFyksLvL&md5=03273a1c14d5c0c29089fc27311917c9CAS | open url image1

[6]  A. P. Liesen, A. T. Silva, J. C. Sousa, P. H. Menezes, R. A. Oliveira, Tetrahedron Lett. 2012, 53, 4240.
         | CrossRef | 1:CAS:528:DC%2BC38Xps1Kgtbg%3D&md5=ecf97e65f5c45b126579b3c2df05ac92CAS | open url image1

[7]  T. Habu, N. Mii, K. Kuge, H. Manto, Y. Takamuki, J. Imaging Sci. 1991, 35, 202.
         | 1:CAS:528:DyaK3MXlt1eltL4%3D&md5=1052247e6ad197e3854c706d784191abCAS | open url image1

[8]  A. H. Davulcu, D. D. McLeod, J. Li, K. Katipally, A. Littke, W. Doubleday, Z. M. Xu, C. W. McConlogue, C. J. Lai, M. Gleeson, M. Schwinden, R. L. Parsons, J. Org. Chem. 2009, 74, 4068.
         | CrossRef | 1:CAS:528:DC%2BD1MXkvFeku70%3D&md5=df039e475898c284cbcac5c62b243019CAS | open url image1

[9]  D. M. Zimmerman, R. A. Olofson, Tetrahedron Lett. 1969, 10, 5081.
         | CrossRef | open url image1

[10]  W. G. Finnegan, R. A. Henry, E. Lieber, J. Org. Chem. 1953, 18, 779.
         | CrossRef | 1:CAS:528:DyaG2cXjvFWksw%3D%3D&md5=e036461f9425831a0e277d2fe731326cCAS | open url image1

[11]  D. Habibi, M. Nasrollahzadeh, L. Mehrabi, S. Mostafaee, Monatsh. Chem. 2013, 144, 725.
         | CrossRef | 1:CAS:528:DC%2BC3sXmtVWlsbo%3D&md5=c1b7dc20ff7e6aa09f01de68be651243CAS | open url image1

[12]  A. R. Kazemizadeh, N. Hajaliakbarib, R. Hajianb, N. Shajaria, A. Ramaza, Helv. Chim. Acta 2012, 95, 594.
         | CrossRef | 1:CAS:528:DC%2BC38XlsFSnurs%3D&md5=e46fea83d3f18d215d948b8d37cbd923CAS | open url image1

[13]  P. Mani, A. K. Singh, S. K. Awasthi, Tetrahedron Lett. 2014, 55, 1879.
         | CrossRef | 1:CAS:528:DC%2BC2cXjtVGgu74%3D&md5=8a4b803695255499c3f7f03343873318CAS | open url image1

[14]  M. Parveen, F. Ahmad, A. M. Malla, S. Azaz, New J. Chem. 2015, 39, 2028.
         | CrossRef | 1:CAS:528:DC%2BC2MXmtleiuw%3D%3D&md5=3ff5b0d9e55fe4fa86e51439546654fdCAS | open url image1

[15]  A. Kumar, R. Narayanan, H. Shechter, J. Org. Chem. 1996, 61, 4462.
         | CrossRef | 1:CAS:528:DyaK28XktFygtrc%3D&md5=444543bf287eb57ee7654b96007fe8b2CAS | open url image1

[16]  S. Hajra, D. Sinha, M. Bhowmick, J. Org. Chem. 2007, 72, 1852.
         | CrossRef | 1:CAS:528:DC%2BD2sXhtlemtLo%3D&md5=d2d727bf7c55f5656c649d769c693f87CAS | open url image1

[17]  M. Nikoorazm, A. Ghorbani-Choghamarani, M. Khanmoradi, Appl. Organomet. Chem. 2016, 30, 705.
         | CrossRef | 1:CAS:528:DC%2BC28XpsF2qu74%3D&md5=f6690fa780478954a41fcc7f970e7ee2CAS | open url image1

[18]  A. Ghorbani-Choghamarani, L. Shiri, G. Azadi, RSC Adv. 2016, 6, 32660. open url image1

[19]  D. Habibi, M. Nasrollahzadeh, Y. Bayat, Synth. Commun. 2011, 41, 2135.
         | CrossRef | 1:CAS:528:DC%2BC3MXmtl2ltLw%3D&md5=2a01f7245d31199328721548ffe4eb93CAS | open url image1

[20]  G. Venkateshwarlu, A. Premalatha, K. C. Rajanna, P. K. Saiprakash, Synth. Commun. 2009, 39, 4479.
         | CrossRef | 1:CAS:528:DC%2BD1MXhsVKitL7K&md5=60a9461daa794f368a145b64fa984107CAS | open url image1

[21]  A. N. Chermahini, A. Teimouri, F. Momenbeik, A. Zarei, Z. Dalirnasab, A. Ghaedi, M. Roosta, J. Heterocycl. Chem. 2010, 47, 913.
         | CrossRef | 1:CAS:528:DC%2BC3cXps1GisLw%3D&md5=a22697888348968482df171f8f425d71CAS | open url image1

[22]  M. Zaarour, M. El Roz, B. Dong, R. Retoux, R. Aad, J. Cardin, C. Dufour, F. Gourbilleau, J.-P. Gilson, S. Mintova, Langmuir 2014, 30, 6250.
         | CrossRef | 1:CAS:528:DC%2BC2cXns1CmsLc%3D&md5=3a3e5f9866f3f3b482dcce71fc878cecCAS | open url image1

[23]  R. Kou, Y. Shao, D. Mei, Z. Nie, D. Wang, C. Wang, J. Liu, J. Am. Chem. Soc. 2011, 133, 2541.
         | CrossRef | 1:CAS:528:DC%2BC3MXhs1Cqurs%3D&md5=9552970cd167b18dad477c3476cb6bfdCAS | open url image1

[24]  C. M. Crudden, M. Sateesh, R. Lewis, J. Am. Chem. Soc. 2005, 127, 10045.
         | CrossRef | 1:CAS:528:DC%2BD2MXltlyrtrc%3D&md5=2c7cbe42a42ef0d0bc43db33a05cdfe6CAS | open url image1

[25]  M. Egashira, H. Takatsuji, S. Okada, J. Yamaki, J. Power Sources 2002, 107, 56.
         | CrossRef | 1:CAS:528:DC%2BD38XisFyqt7c%3D&md5=ab022519769bc043307b37580ff70a3bCAS | open url image1

[26]  B. Xue, P. Chen, Q. Hong, J. Lin, K. L. Tan, J. Mater. Chem. 2001, 11, 2378.
         | CrossRef | 1:CAS:528:DC%2BD3MXms1Ckt7g%3D&md5=6f3e0de63e3820f734fcf815f6281400CAS | open url image1

[27]  A. Ghorbani-Choghamarani, Z. Taherinia, RSC Adv. 2016, 6, 9410. open url image1

[28]  S. Zhang, Biotechnology 2004, 22, 151.
         | 1:CAS:528:DC%2BD2cXnvFaqtQ%3D%3D&md5=3c29e6c450fda994201b6c39da291aceCAS | open url image1

[29]  H. Zhao, Y. Wei, J. Xu, J. Kan, W. Su, M. Hong, J. Org. Chem. 2011, 76, 882.
         | CrossRef | 1:CAS:528:DC%2BC3MXjvFKgtw%3D%3D&md5=e4fe083ab82953b0a4181bf710b27aedCAS | open url image1

[30]  Z. Duan, S. Ranjit, P. Zhang, X. Liu, Chem. – Eur. J. 2009, 15, 3666.
         | CrossRef | 1:CAS:528:DC%2BD1MXksleisLw%3D&md5=babd29a6092730b616e7a86a608bcc97CAS | open url image1

[31]  S. Bhadra, W. Dzik, L. Gooßen, Angew. Chem. Int. Ed 2013, 52, 2959.
         | CrossRef | 1:CAS:528:DC%2BC3sXhvVGnurg%3D&md5=4eb5377e9516d3eb7205b73cc7710944CAS | open url image1

[32]  Y. Zhang, S. Patel, N. Mainolfi, Chem. Sci. 2012, 3, 3196.
         | CrossRef | 1:CAS:528:DC%2BC38XhsVGhsrzJ&md5=a2c38a262378bf114074d12354d0a4e3CAS | open url image1

[33]  W. Xin, D. Zhu, G. Liu, Y. Hua, W. Zhou, Int. J. Photoenergy 2012, 2012, 767905.
         | CrossRef | open url image1

[34]  C. Anitha, C. D. Sheela, P. Tharmaraj, R. Shanmugakala, Int. J. Inorg. Chem. 2012, 2012, 7. open url image1

[35]  A. Najafi Chermahini, M. K. Omran, H. A. Dabbagh, G. Mohammadnezhad, A. Teimouri, New J. Chem. 2015, 39, 4814.
         | CrossRef | 1:CAS:528:DC%2BC2MXmt1WqsLo%3D&md5=de431e254efaa98b7231d5a21be50b5fCAS | open url image1

[36]  I. Esirden, E. Basar, M. Kaya, Chem. Pap. 2015, 69, 1231.
         | CrossRef | 1:CAS:528:DC%2BC2MXps1Oksrs%3D&md5=558dfbe55055d22cabbf44411db88a12CAS | open url image1

[37]  L. Zamani, B. B. F. Mirjalili, K. Zomorodian, S. Zomorodian, S. Afr, J. Chem. 2015, 68, 133.
         | 1:CAS:528:DC%2BC2MXhvVaksb3K&md5=811d462ac8bbf5e793000e266f4c46a2CAS | open url image1

[38]  H. M. Nanjundaswamy, H. Abrahamse, Heterocycles 2014, 89, 2137.
         | CrossRef | 1:CAS:528:DC%2BC2cXhvVOrtr7F&md5=a777c75022c4f345127f37124215e705CAS | open url image1

[39]  X. Guo, H. Rao, H. Fu, Y. Jiang, Y. Zhao, Adv. Synth. Catal. 2006, 348, 2197.
         | CrossRef | 1:CAS:528:DC%2BD28XhtFygu7zF&md5=c8083e6456639ae2c9ed58e4a3e316aaCAS | open url image1

[40]  Q. Zhang, C. Liu, J. Shi, Q. Xu, L. Jin, C. Zhao, T. Zhang, Synlett 2016, 27, 1945.
         | CrossRef | 1:CAS:528:DC%2BC28XntlKgsbc%3D&md5=0ce642cfc3e877d72afc599f07496905CAS | open url image1

[41]  R. A. Altman, K. W. Anderson, S. L. Buchwald, J. Org. Chem. 2008, 73, 5167.
         | CrossRef | 1:CAS:528:DC%2BD1cXntVyns7Y%3D&md5=dfd6c49e426f8a58919671c81db13f3aCAS | open url image1

[42]  L. Ackermann, R. Sandmann, W. Song, Org. Lett. 2011, 13, 1784.
         | CrossRef | 1:CAS:528:DC%2BC3MXisFWlt7Y%3D&md5=7f02115a6298849707521afaa3134f8cCAS | open url image1

[43]  N. S. Nandurkar, M. J. Bhanushali, M. D. Bhor, B. M. Bhanage, Tetrahedron Lett. 2007, 48, 6573.
         | CrossRef | 1:CAS:528:DC%2BD2sXpt1eqtb8%3D&md5=34c6a769a3c7f8170dc22fd570d3ca12CAS | open url image1

[44]  M. A. Carroll, R. A. Wood, Tetrahedron 2007, 63, 11349.
         | CrossRef | 1:CAS:528:DC%2BD2sXhtFeltL%2FE&md5=a8e9f946062a095a657ff007ca9d1a1cCAS | open url image1

[45]  L. Rout, P. Saha, S. Jammi, T. Punniyamurthy, Adv. Synth. Catal. 2008, 350, 395.
         | CrossRef | 1:CAS:528:DC%2BD1cXltFOjs7s%3D&md5=94e5e8fbe821d79bf3c1829382f905e7CAS | open url image1

[46]  F. Y. Kwong, A. Klapars, S. L. Buchwald, Org. Lett. 2002, 4, 581.
         | CrossRef | 1:CAS:528:DC%2BD38XlsVCqsg%3D%3D&md5=7048eafdcc39c50e74450d9c33e39b7fCAS | open url image1

[47]  P. Spagnolo, P. Zanirato, J. Chem. Soc., Perkin Trans. 1 1988, 2615.
         | CrossRef | 1:CAS:528:DyaL1MXpsFWisg%3D%3D&md5=29b8e26976493b2c19b759a84e6d4f8cCAS | open url image1

[48]  H. Rao, H. Fu, Y. Jiang, Y. Zhao, J. Org. Chem 2005, 70, 8107.
         | CrossRef | 1:CAS:528:DC%2BD2MXpt1WhtLs%3D&md5=7e799770652a11d1be17c14951479b05CAS | open url image1

[49]  D. Maiti, B. P. Fors, J. L. Henderson, Y. Nakamura, S. L. Buchwald, Chem. Sci. 2011, 2, 57.
         | CrossRef | 1:CAS:528:DC%2BC3cXhsFWqsbjF&md5=3f59997b9be0c7c546896ef75187722fCAS | open url image1

[50]  S. Miyano, N. Abe, A. Uno, Chem. Pharm. Bull. 1966, 14, 731.
         | CrossRef | 1:CAS:528:DyaF2sXit12i&md5=7faad3bccad1e98290122e9a105d07f7CAS | open url image1

[51]  M. Abdollahi Alibeik, A. Moaddeli, New J. Chem. 2015, 39, 2116.
         | CrossRef | 1:CAS:528:DC%2BC2cXitFOgtbjF&md5=2bd258ec51daeda8e2959e5066993ab0CAS | open url image1

[52]  M. Zarghani, B. Akhlaghinia, RSC Adv. 2015, 5, 87769.
         | CrossRef | 1:CAS:528:DC%2BC2MXhsFOrt77I&md5=c3aae9710fd135e234d878457777af19CAS | open url image1



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