Regioselective ring opening of epoxides with thiols under solvent free and mild conditions using heterogeneous catalyst

Bandgar, B. P.; Patil, Abasaheb V.; Chavan, Omprakash S.; Kamble, Vinod T.

doi:10.1016/j.catcom.2006.10.003

Cited by 27 publications

(5 citation statements)

References 30 publications

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“…This reaction also is of practical interest, and especially a heterogeneous catalyst for converting this readily available, inexpensive epoxide to β-alkoxyalcohol, which is a valuable synthetic intermediate for 1,2-diol and 1,2-diol mono-ether organic syntheses is highly desirable. 26 Current processes often suffer from long reaction times, drastic reaction conditions, unsatisfactory conversion and poor regioselectivity.…”

Section: Ring Opening Reactions Of Styrene Oxide With Methanolmentioning

confidence: 99%

Cr-MIL-101 encapsulated Keggin phosphotungstic acid as active nanomaterial for catalysing the alcoholysis of styrene oxide

et al. 2014

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Mesoporous chromium-based terephthalate metal-organic framework (MIL-101) encapsulated Keggin phosphotungstic acid (HPW) ] was demonstrated to be an active heterogeneous catalyst for selective catalysis of the ring opening reaction of styrene oxide with methanol achieving 99 % yield of 2-methoxy-2-phenylethanol in 20 minutes at 40 °C. Similar MIL-101 samples prepared using one-pot microwave synthesis in the absence of HPW or in the presence of hydrofluoric acid (HF) were less active. The impact of fluoride and HPW polyanions incorporation on the acidity of MIL-101 was investigated by in situ Infrared spectroscopy technique using CO as a probe molecule. Additional hydroxyl groups and Lewis acid sites are present in MIL-101(HPW) explaining the observed superior catalytic performance in styrene oxide methanolysis. IntroductionMetal-organic frameworks (MOFs) are a rapidly growing family of organic-inorganic hybrid materials built from organic ligands bridging metal ions.1 By systematic design and fine-tuning, MOF structures having high accessible porosity and pores with dimensions in the range of several angstroms to nanometres have been achieved.2 These unique and outstanding features of MOFs imparted for a vast range of promising potential applications such as gas storage,

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Section: Ring Opening Reactions Of Styrene Oxide With Methanolmentioning

confidence: 99%

Cr-MIL-101 encapsulated Keggin phosphotungstic acid as active nanomaterial for catalysing the alcoholysis of styrene oxide

et al. 2014

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“…To show the merit of the present work, we compared the results of NiFe 2 O 4 @SiO 2 -PPA in the N-formylation of aniline with formic acid to other protic acids immobilized on silica gel, like HClO 4 -SiO 2 [20], H 2 SO 4 -SiO 2 [29], HBF 4 -SiO 2 [30], and TFA-SiO 2 [31]. All the catalysts were tested at the same catalytic loading.…”

Section: The Catalytic Application Of Nife 2 O 4 @Sio 2 -Ppa In Nform...mentioning

confidence: 99%

Polyphosphoric acid supported on silica-coated NiFe2O4 nanoparticles: An efficient and magnetically-recoverable catalyst for N-formylation of amines

Khojastehnezhad

Rahimizadeh

Moeinpour

et al. 2013

Comptes Rendus. Chimie

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“…They can be easily cleaved with different nucleophiles to give regio and stereoselective products [2,15,16]. Recently, various methods have been reported using metal triflates [17,18] and some heterogeneous catalysts [19,20]. However, there are some limitations with these, such as poor yields and regioselectivity, the use of air, moisture-sensitive catalysts, requirement of stoichiometric amounts of catalyst and problems in the recovery of the catalysts.…”

Section: Introductionmentioning

confidence: 97%

Theoretical and Experimental Studies on the Regioselectivity of Epoxide Ring Opening by Nucleophiles in Nitromethane without any Catalyst: Nucleophilic-Chain Attack Mechanism

Mohseni

Bakavoli

Morsali

2014

Progress in Reaction Kinetics and Mechanism

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We describe here a mild and efficient method for the nucleophilic ring-opening of epoxides with amines, alcohols and water in the presence of nitromethane as a polar solvent without using any catalyst. The reactions are highly regioselective and afford the products in excellent yields within a short period of time at room temperature. The regioselectivity for this ring opening has been investigated using experimental and theoretical 1 H and 13 C NMR studies together with activation energy calculations at the B3LYP/6-311+G(2d,p) level of theory. The mechanism of nucleophilic attack has been investigated in terms of a direct attack or a methanol chain attack.

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Regioselective ring opening of epoxides with thiols under solvent free and mild conditions using heterogeneous catalyst

Cited by 27 publications

References 30 publications

Cr-MIL-101 encapsulated Keggin phosphotungstic acid as active nanomaterial for catalysing the alcoholysis of styrene oxide

Cr-MIL-101 encapsulated Keggin phosphotungstic acid as active nanomaterial for catalysing the alcoholysis of styrene oxide

Polyphosphoric acid supported on silica-coated NiFe2O4 nanoparticles: An efficient and magnetically-recoverable catalyst for N-formylation of amines

Theoretical and Experimental Studies on the Regioselectivity of Epoxide Ring Opening by Nucleophiles in Nitromethane without any Catalyst: Nucleophilic-Chain Attack Mechanism

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