Abstract
N-Aryl acetamides synthesis from the corresponding nitro compounds via a reductive N-acetylation was achieved over Pd supported on Sn modified Al2O3 catalyst using H2, acetic anhydride as acetylating agent in aqueous media at ambient temperature. The pyridine-IR data demonstrated a majority of Lewis acid sites compared to Brønsted acid sites on the catalyst surface. Pyridine-IR and CO pulse chemisorption results emphasized a combination of surface palladium in conjunction with Lewis acid sites were responsible for the high activity of 2wt%Pd/5wt%Sn–Al2O3 over 2wt%Pd/Al2O3 catalyst with consistent activity and selectivity for four recycles. The bulk and surface properties of the catalysts were characterized by BET-SA, XRD, XPS, TPD of NH3, H2-TPR, CO pulse chemisorption, TEM and the promotional effect of surface Lewis acid sites are rationalized by in situ pyridine adsorbed DRIFT spectroscopy.
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Yang S, Li B, Wan X, Shi Z (2007) J Am Chem Soc 129:6066–6067
Watanabe Y, Tsuji Y, Kondo T, Takeuchi R (1984) J Org Chem 49:4451–4455
Scriven EFV, Turnbull K (1988) Chem Rev 88:297–368
Lee SY, Lee CW, Oh DY (1999) J Org Chem 64:7017–7022
Wang B, Jiang C, Qian J, Zhang S, Jia X, Yuan Y (2018) Org Biomol Chem 16:101–107
Beckett AH, Daisley RW, Walker J (1968) Tetrahedron 24:6093–6109
Koletzel MC, Herzog HL (1950) J Org Chem 15:370–373
Kim BH, Han R, Piao F, Jun YM, Baik W, Lee BM (2003) Tetrahedron lett 44:77–79
Zand Z, Kazemi F, Partovi A (2015) J Photochem Photobiol B 152:58–62
Shokri Z, Zeynizadeh B, Hosseini SA (2017) J Colloid Interface Sci 485:99–105
Rahaim RJ, Maleczka RE (2006) Synthesis 19:3316–3340
Kantam ML, Reddy RS, Srinivas K, Chakravarti R, Sreedhar B, Figueras F, Reddy CV (2012) J Mol Catal A Chem 355:96–101
Nahmed EM, Jenner G (1991) Tetrahedron Lett 32:4917–4920
Landesberg JM, Katz L, Olsen C (1972) J Org Chem 37:930–936
Benedetti A, Fagherazzi G, Pinna F, Rampazzo G, Selva M, Strukul G (1991) Catal Lett 10:215–223
Du W, Mackenzie KE, Milano FD, Deskins NA, Su D, Teng X (2012) ACS Catal 2:287–297
Collins G, Blomker M, Osiak M, Holmes JD, Bredol M, O’Dwyer C (2013) Chem Mater 25:4312–4320
Tong DS, Zhou CH, Li MY, Yu WH, Beltramini J, Lin CX, Xu ZP (2010) Appl Clay Sci 48:569–574
Haan JL, Stafford KM, Masel RI (2010) J Phys Chem C 114:11665–11672
Sa J, Gasparovicova D, Hayek K, Halwax E, Anderson JA, Vinek H (2005) Catal Lett 105:209–217
Kobayashi S, Manabe K (2002) Acc Chem Res 35:209–217
He S, Sun C, Bai Z, Dai X, Wang B (2009) Appl Catal A Gen 356:88–98
Vishali B, Venu B, Kumar VV, Naresh G, Sudhakar M, Venugopal A (2017) J Phys Chem C 121:22191–22198
Burch R (1981) J Catal 71:348–359
Knozinger H, Ratnasamy P (1978) Catal Rev 17:31–70
Scotti N, Dangate M, Gervasini A, Evangelisti C, Ravasio N, Zaccheria F (2014) ACS Catal 4:2818–2826
Venu B, Vishali B, Kumar VV, Naresh G, Sreedhar I, Venugopal A (2018) Mol Catal 445:43–51
Fondell M, Gorgoi M, Boman M, Lindblad A (2014) J Electron Spectrosc Relat Phenom 195:195–199
Aytam HP, Akula V, Janmanchi K, Kamaraju SRR, Panja KR (2002) J Phys Chem B 106:1024–1031
Gao Y, Ma D, Wang C, Guana J, Bao X (2011) Chem Commun 47:2432–2434
Li H, Zhao Q, Wan Y, Dai W, Qiao M (2006) J Catal 244:251–254
Mahata N, Cunha AF, Orfao JJM, Figueiredo JL (2008) Appl Catal A Gen 351:204–209
Serna P, Lopez-Haro M, Calvino JJ, Corma A (2009) J Cata 263:328–334
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BS thank UGC New Delhi for the award of fellowship. There is no conflict of interest pertaining to the results presented in this paper.
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Bilakanti, V., Gutta, N., Velisoju, V.K. et al. Understanding the role of surface Lewis acid sites of Sn modified Pd/Al2O3 catalyst in the chemoselective reductive N-acetylation of nitrobenzene. Reac Kinet Mech Cat 130, 347–362 (2020). https://doi.org/10.1007/s11144-020-01765-0
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DOI: https://doi.org/10.1007/s11144-020-01765-0