Abstract
A novel, air stable, water dispersible and efficient catalyst based on copper nanoparticles immobilized on nitrogen doped carbons derived from inorganic–organic composite [Cu(0)@NDC-Sil] has been prepared. Doping of carbons i.e. inorganic–organic (silica–starch) composite using 5-phenyl-1,2,3,4-tetrazole, a nitrogen-rich precursor imparts a variety of nitrogen functionalities even at moderate temperature and enables the generation of active sites for the immobilization of Cu(0) nanoparticles. The novel catalyst system has been well characterized by various techniques like SEM, HRTEM, STEM, TGA, CHN, EDX, ICP-AES, XRD and XPS and was found to be highly efficient for the one-pot synthesis of 1,4-disubstituted-1,2,3-triazoles via click chemistry approach with a wide range of substrate scope such as benzyl/allyl halides and alkyl bromides. Moreover, it could be easily recovered by filtration and reused without significant loss in its activity.
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Deng Y, Xie Y, Zou K, Ji X (2016) J Mater Chem A 4:1144
Li XL, Wang HL, Robinson JT, Sanchez H, Diankov G, Dai HJ (2009) J Am Chem Soc 131:15939
Lin ZY, Waller G, Liu Y, Liu ML, Wong CP (2012) Adv Energy Mater 2:884
Sheng ZH, Shao L, Chen JJ, Bao WJ, Wang FB, Xia XH (2011) ACS Nano 5:4350
Hou SC, Cai X, Wu HW, Yu X, Peng M, Yan K, Zou DC (2013) Energy Environ Sci 6:3356
Choi CH, Chung MW, Park SH, Woo SI (2013) RSC Adv 3:4246
Mao Y, Duan H, Xu B, Zhang L, Hu Y, Zhao C, Wang Z, Chen L, Yang Y (2012) Energy Environ Sci 5:7950
Li R, Cao A, Zhang Y, Li G, Jiang F, Li S, Chen D, Wang C, Ge J, Shu C (2014) ACS Appl Mater Interfaces 6:20574
Liu D, Chen X, Xu G, Guan J, Cao Q, Dong B, Qi Y, Li C, Mu X (2016) Sci Rep 6:21365
Agalave SG, Maujan SR, Pore VS (2011) Chem Asian J 6:2696
Amini M, Hassandoost R, Bagherzadeh M, Gautam S, Chae KH (2016) Catal Commun 85:13
Haldon E, Nicasio MC, Perez PJ (2015) Org Biomol Chem 13:9528
Chanda K, Rej S, Huang MH (2013) Chem Eur J 19:16036
Tsai Y-H, Chanda K, Chu Y-T, Chiu C-Y, Huang MH (2014) Nanoscale 6:8704
Rej S, Chanda K, Chiu C-Y, Huang MH (2014) Chem Eur J 20:15991
Madasu M, Hsia C-F, Huang MH (2017) Nanoscale 9:6970
Beneteau V, Olmos A, Boningari T, Sommer J, Pale P (2010) Tetrahedron Lett 51:3673
El-bendary MM, Saleh TS, Al-Bogami AS (2018) Catal Lett 148:3797
Nasrollahzadeh M, Jaleh B, Fakhri P, Zahraei A, Ghadery E (2015) RSC Adv 5:2785
Mishra A, Rai P, Srivastava M, Tripathi BP, Yadav S, Singh J, Singh J (2017) Catal Lett 147:2600
Bihani M, Pasupuleti BG, Bora PP, Bez G, Lal RA (2018) Catal Lett 148:1315
Yu WB, Jiang LX, Shen C, Xu WM, Zhang PF (2016) Catal Commun 79:11
Wan L, Cai C (2012) Catal Lett 142:1134
Salamatmanesh A, Miraki MK, Yazdani E, Heydari A (2018) Catal Lett 148:3257
Jahanshahia R, Akhlaghinia B (2016) RSC Adv 6:29210
Sharma H, Mahajan H, Jamwal B, Paul S (2018) Catal Commun 107:68
Bhardwaj M, Kour M, Paul S (2016) RSC Adv 6:99604
Demko PZ, Sharpless KB (2001) J Org Chem 66:7945
Han X, He X, Sun L, Han X, Zhan W, Xu J, Wang X, Chen J (2018) ACS Catal 8:3348
Qian Y, Du P, Wu P, Cai C, Gervasio DF (2016) J Phys Chem C 120:9884
Blonski P, Tucek J, Sofer Z, Mazanek V, Petr M, Pumera M, Otyepka M, Zboril R (2017) J Am Chem Soc 139:3171
Eisenberg D, Slot TK, Rothenberg G (2018) ACS Catal 8:8618
Fiorio JL, Gonçalves RV, Teixeira-Neto E, Ortuno MA, Lopez N, Rossi LM (2018) ACS Catal 8:3516
Zhang R, Sun Z, Feng R, Lin Z, Liu H, Li M, Yang Y, Shi R, Zhang W, Chen Q (2017) ACS Appl Mater Interfaces 9:38419
Sahraie NR, Paraknowitsch JP, Gobel G, Thomas A, Strasser P (2014) J Am Chem Soc 136:14486
Zheng L, Zheng S, Wei H, Du L, Zhu Z, Chen J, Yang D (2019) ACS Appl Mater Interfaces 11:6248
Zhou W, Xiong T, Shi C, Zhou J, Zhou K, Zhu N, Li L, Tang Z, Chen S (2016) Angew Chemie Int Ed 128:8556
Hu Y, Zhang H, Wu P, Zhang H, Zhou B, Cai C (2011) Phys Chem Chem Phys 13:4083
Kumar BSPA, Reddy KHV, Madhav B, Ramesh K, Nageswar YVD (2012) Tetrahedron Lett 53:4595
Vantikommu J, Palle S, Reddy PS, Ramanatham V, Khagga M, Pallapothula VR (2010) Eur J Med Chem 45:5044
Albadi J, Keshavarz M, Shirini F, Vafaie-nezhad M (2012) Catal Commun 27:17
Acknowledgements
We thank the Head, ACMS, IIT Kanpur for XPS study; Head, SAIF, IIT Bombay for ICP-AES, HR-TEM, STEM and CHN studies; AMRC, IIT Mandi for SEM, EDX and PXRD studies. Financial assistance to authors [CS (JRF, UGC) and MK (JRF, CSIR)] is gratefully acknowledged.
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Sharma, C., Kaur, M., Choudhary, A. et al. Nitrogen Doped Carbon–Silica Based Cu(0) Nanometal Catalyst Enriched with Well-Defined N-moieties: Synthesis and Application in One-Pot Synthesis of 1,4-Disubstituted-1,2,3-triazoles. Catal Lett 150, 82–94 (2020). https://doi.org/10.1007/s10562-019-02936-y
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DOI: https://doi.org/10.1007/s10562-019-02936-y