PEG-SO3H: A mild and efficient recyclable catalyst for the synthesis of coumarin derivatives

Abstract

A simple and efficient synthesis of coumarin derivatives through condensation reaction of substituted phenols and dicarbonyl compounds using PEG-SO 3 H as a recyclable catalyst under solvent-free conditions is described.

Sulfonated polyethylene glycol (PEG-OSO3H) as a polymer supported biodegradable and recyclable catalyst in green organic synthesis: recent advances

“…Thus, Nazeruddin and co-workers have described a high yielding synthesis of coumarin derivatives through condensation reaction of substituted phenols and dicarbonyl compounds using PEG-OSO 3 H as a biodegradable recyclable catalyst under solvent-free conditions at the 80 C (Scheme 7). 102 The authors have compare the activity of various catalysts such as silica sulfuric acid, SnCl 2 , BF 3 $SiO 2 , PEG and PEG-OSO3H in Pechmann condensation of resorcinol and methyl acetoacetate in ratio (1 : 1.1). Excellent yield of the desired product was obtained when PEG-OSO 3 H was used as a catalyst.…”

Heterogeneously Catalyzed Pechmann Condensation Employing the Tailored Zn0.925Ti0.075O NPs: Synthesis of Coumarin

“…Various catalysts such as mineral acids like H 2 SO 4 , HCl, H 3 PO 4 , CF 3 COOH, HClO 4, ClSO 3 H, PTSA, and oxalic acid as well as Lewis acids such as ZnCl 2 , FeCl 3 , SnCl 4 , SnCl 2 ·H 2 O, TiCl 4 , AlCl 3 , ZrCl 4, InCl 3 , BiCl 3 , Sm(NO 3 ) 3 , BF 3 ·H 2 O, CAN, Cu(ClO 4 ) 2 , BaCl 2 , and NbCl 5 were also reported in the conventional synthesis of coumarin via Pechmann condensation. 13 Similarly, different heterogeneous catalysts were also employed for Pechmann condensation such as Al-MCM-41, 14 Al-SBA-1 molecular sieves, 15 Keggin structures heteropolyacids, 16 graphite-montmorillonite K10, 17 H 14 [NaP 5 W 30 O 110 ], 18 silica triflate, 19 mesoporous zirconium phosphate, 20 ZrOCl 2 ·8H 2 O/SiO 2 , 21 pentafluorophenylammonium triflate, 22 periodic mesoporous silica chloride, 23 melamine–formaldehyde resin-supported H + , 24 PEG-SO 3 H, 25 poly(4-vinylpyridinium) hydrogen sulfate, 26 PVP-supported phosphotungstic acid, 27 poly(4-vinylpyridine)-supported copper iodide, 28 1-butyl-3-methylimidazolium chloroaluminate, and 1-butyl-3-methylimidazolium hexafluorophosphate ionic liquid. 29…”

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“…For example as illustrated in Scheme 28, the ultrasonic-aided reaction has demonstrated between the and phenol-based chemicals [69,70].…”