ZSM-5-SO3H as a novel, efficient, and reusable catalyst for the chemoselective synthesis and deprotection of 1,1-diacetates under eco-friendly conditions

Abstract

ZSM-5 has been modified as supported sulfuric acid (ZSM-5-SO 3 H) and introduced for the first time as a mild, convenient, reusable, and heterogeneous catalyst. Various types of aldehydes were efficiently converted to their 1,1-diacetates using a catalytic amount of ZSM-5-SO 3 H in excellent yields under solvent-free and heterogeneous conditions at room temperature. The deprotection of 1,1-diacetates has also been achieved using this novel catalyst in ethanol. The procedure is operationally simple, environmentally benign, and only a stoichiometric amount of anhydride is used.

Highly Selective Synthesis of β-Amino Carbonyl Compounds over ZSM-5-SO3H under Solvent-free Conditions

“…This catalyst has been characterized by SEM, XRD, FTIR and BET techniques. 18 In this work, one-pot three-component Mannich reaction of aldehydes, anilines, and ketones over ZSM-5-SO 3 H as catalyst, has been studied. The effect of different parameters on the synthesis of various β-aminocarbonyl compounds was investigated.…”

“…18 Herein, we wish to report, three-component diastereo-controlled Mannich reaction catalyzed by a ZSM-5-SO 3 H under solvent-free conditions.…”

Synthesis of 2-hydroxy-1,4-naphthoquinone derivatives via a three-component reaction catalyzed by nanoporous MCM-41

“…In order to overcome the lower reaction rate of heterogeneous catalysts compared to homogeneous ones, the use of high surface area materials such as nanoporous MCMs, SBAs, and zeolites have been widely investigated [6][7][8][9].…”

Microwave-assisted green synthesis of 1,1-diacetates (acylals) using selectfluor™ as an environmental-friendly catalyst under solvent-free conditions

“…Therefore, the methods for their synthesis have received considerable attention. Usually, the preparation of 1,1-diacetates has been achieved by the reaction of aldehydes with acetic anhydride in the presence of different catalysts and under microwave irradiation such as SBA-15-Ph-PrSO 3 H [6], Fe 3 O 4 @SiO 2 [7], PEG-SO 3 H [8], Poly(4-vinylpyridinium) perchlorate [9], TiCl 4 [10], N-Sulfonic acid poly(4-vinylpyridinum) hydrogen sulfate [11], NaHSO 4 -SiO 2 [12], H 2 SO 4 -silica [13], SbCl 3 [14], 1,3-Dibromo-5,5-dimethylhydantoin [15], Silica-supported functional ionic liquid (Si- [SbSipim][PF6]) [16], ZSM-5-SO 3 H [17], Amberlyst-15 [18], Zirconium hydrogen sulfate [19] Bismuth triflate [20], Iron(III) fluoride [21] and etc. Although some of these methods 1,1-diacetates are obtained in good to high product yields suffer from some disadvantages such as long reaction time, require high temperature, tedious work-up procedure, the use of homogenous catalysts or harmful solvents, expensive and highly toxic catalysts and involve strongly acidic or oxidizing conditions.…”