Document Type: Original Research Article

Authors

1 Department of Chemistry, Payame Noor University, 19395-4697 Tehran, Iran

2 Chemistry Department, Qaemshahr Branch, Islamic Azad University, P. O. Box 163, Qaemshahr, Iran

3 School of Chemistry, Shahrood University of Technology, Shahrood, Iran

Abstract

In this study, an efficient and simple procedure is reported for the chemoselctive acetylation of various aldehydes (aromatic and aliphatic) with acetic anhydride by 1,1'‐butylenebispyridinium hydrogen sulfate (Bbpy)(HSO4)2as a green and halogen-free catalyst under solvent-free conditions at room temperature. The selective conversion of the aldehydes was observed in the presence of ketones, and the deprotection of 1,1-diacetates has also been achieved using (Bbpy)(HSO4)2in water as a green solvent in reflux conditions. This procedure has valuable advantages including short reaction times, simple workup, high yields of products, absence of solvent, and use of commercially available and non-toxic reagents.

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[1]. Kochhar K.S., Bal B.S., Deshpande R.P., Rajadhyaksha S.N., Pinnick H.W. J. Org. Chem., 1983, 48:1765

[2]. Frick J.G., Harper R.J. J. Appl. Polym. Sci., 1984, 29:1433

[3]. Shelke K., Sapkal S., Kategaonkar A., Shingate B., Shingare M.S. South Afr. J. Chem., 2009, 62:109

[4]. Van-Heerden F.R., Huyser J.J., Bardley D., Williams G., Holzapfel C.W. Tetrahedron Lett., 1998, 39:5281

[5]. Andberg M., Sydness L.K. Tetrahedron Lett., 1998, 39:6361

[6]. Ullah Bhat S., Naikoo R., Tomar R., Ahmad Bhat R., Malla M., Kumar N., Tiwari K. Asian J. Green Chem., 2017, 1:46

[7]. Esmaeilpour M., Sardarian A.R., Javidi J. Appl. Catal., A., 2012, 445–446:359

[8]. Zong Y.X., Wang J.K., Niu Y.Y., Li Z.L., Song Z.E., Quan Z.J., Wang X.C., Yue G.R., Pan Y. Chin. Chem. Lett., 2013, 24:140

[9]. Ghaffari-Khaligh N. Chin. J. Catal., 2014, 35:329

[10]. Rezayati S., Erfani Z., Rezayati S., Hajinasiri R., Rekavandi M. Iran. Chem. Commun., 2014, 2:72

[11]. Ghaffari-Khaligh N., Ghods Ghasem-Abadi P. Chin. J. Catal., 2014, 35:1126

[12]. Kumar-Kannasani R., Satyanarayana-Peruri V.V., Reddy-Battula S. Chem. Cent. J., 2012, 6:136

[13]. Sajjadifar S., Rezayati S. Chem. Pap., 2014, 68:531

[14]. Rezayati S., Hajinasiri R., Erfani Z. Res. Chem. Intermed., 2016, 42:2567

[15]. Maleki B., Azarifar D., Ghorbani-vaghei R., Veisi H., Hojati S.F., Gholizadeh M., Salehabadi H., Khodaverdian-Moghadam M. Monatsh Chem., 2006, 140:1485

[16]. Kang L.Q., Cai Y.Q., Cheng L. Monatsh Chem., 2013, 144:247

[17]. Rezaee Nezhad E., Sajjadifar S., Abbasi Z., Rezayati S. J. Sci. I. R. Iran, 2014, 25:127

[18]. Reddy A.V., Ravinder K., Reddy V.L.N., Ravinkanth V., Yenkateswarlu Y. Synth. Commun., 2003, 33:1531

[19]. Rezayati S., Sajjadifar S., Hajinasiri R. Iran J Sci Technol Trans Sci., 2015, 39A2:179

[20]. Carrigan M.D., Eash J.K., Oswald M.C., Mohan R.S. Tetrahedron Lett., 2001, 42:8133

[21]. Sajjadifar S., Nasri P. Res Chem Intermed., 2017, 43:6677

[22]. Wilkes J.S. J. Mol. Catal. A, 2004, 214:11

[23]. Zare A., Hasaninejad A., Parhami A., Moosavi-Zare A.R., Khedri F., Parsaee Z.,  Abdolalipoor-Saretoli M., Khedri M., Roshankar M., Deisi H. J. Serb. Chem. Soc., 2010, 75:1315

[24]. Youseftabar-Miri L., Hosseinjani-Pirdehi H. Asian J. Green Chem., 2017, 2:56

[25]. Mohammadi Zeydi M., Mahmoodi N., Ardeshiri Terogeni G. Asian J. Green Chem., 2017, 2:78

[26]. Poyafar F., Fallah-Mehrjardi M., Banitaba S.H. Asian J. Green Chem., 2018, 3:96

[27]. Ghaffari Khaligh N. Chin. J. Catal., 2014, 35:1497

[28]. Rezayati S., Rezaee Nezhad E., Hajinasiri R., Chin. Chem. Lett., 2016, 27:974

[29]. Abbasi Z., Rezayati S., Bagheri M., Hajinasiri R. Chin. Chem. Lett., 2017, 28:75

[30]. Sajjadifar S., Arzehgar Z., Ghayuri A. J. Chin. Chem. Soc., 2018, 65:205

[31]. Rezayati S., Salehi E., Hajinasiri R., Afshari Sharif Abad S. C. R. Chimie., 2017, 20:554

[32]. Rezayati S., Mirzajanzadeh E., Seifournia H., Asian J. Green Chem., 2017, 1:24

[33]. Rezayati S., Sheikholeslami-Farahani F., Rostami-Charati F., Afshari Sharif Abad S. Res. Chem. Intermed., 2016, 42:4097