Zeolite Catalyzed Aromatic Acylation and Related Reaches

Bekkum, H. van; Hoefnagel, A. J.; Koten, Mark A.; Gunnewegh, E.A.; Vogt, A.; Kouwenhoven, Herman W.

doi:10.1016/s0167-2991(08)63279-6

Cited by 73 publications

(19 citation statements)

References 14 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…Because the carbonyl oxygen strongly coordinates to the Lewis acid center [39], hydrolysis of the Lewis acid is necessary for the isolation of the products. In order to overcome this disadvantage, solid Brønsted acids such as H-Beta zeolite [40][41][42][43], H-Y zeolite [42,44,45], H-ZSM-5 [40][41][42][44][45][46][47], HF/Al 2 O 3 [44], and Nafion-H [48], a resin containing the -CF 2 CF 2 SO 3 H group, are used as the catalyst. However, the selectivity for o-and p-hydroxyacetophenone is not high, and in almost all cases the main product is the decomposition product, phenol.…”

Section: Decomposition Of Phenyl Acetate (Equation (3)) [37]mentioning

confidence: 99%

Catalytic Reactions over Halide Cluster Complexes of Group 5–7 Metals

Nagashima

Kamiguchi

Chihara

2014

Metals

View full text Add to dashboard Cite

Halide clusters of Group 5-7 metals develop catalytic activity above 150-250 °C, and the activity is retained up to 350-450 °C by taking advantage of their thermal stability, low vapor pressure, and high melting point. Two types of active site function: the solid Brønsted acid site and a coordinatively unsaturated site that catalyzes like the platinum metals do. Various types of catalytic reactions including new reactions and concerted catalyses have been observed over the clusters: hydrogenation, dehydrogenation, hydrogenolysis, isomerization of alkene and alkyne, and alkylation of toluene, amine, phenol, and thiol. Ring-closure reactions to afford quinoline, benzofuran, indene, and heterocyclic common rings are also catalyzed. Beckmann rearrangement, S-acylation of thiol, and dehydrohalogenation are also catalyzed. Although the majority of the reactions proceed over conventional catalysts, closer inspection shows some conspicuous features, particularly in terms of selectivity. Halide cluster catalysts are characterized by some aspects: cluster counter anion is too large to abstract counter cation from the protonated reactants, cluster catalyst is not poisoned by halogen and sulfur atoms. Among others, cluster catalysts are stable at high temperatures up to 350-450 °C. At high temperatures, apparent activation energy decreases, and hence weak acid can be a catalyst without decomposing reactants. OPEN ACCESSMetals 2014, 4 236

show abstract

Section: Decomposition Of Phenyl Acetate (Equation (3)) [37]mentioning

confidence: 99%

Catalytic Reactions over Halide Cluster Complexes of Group 5–7 Metals

Nagashima

Kamiguchi

Chihara

2014

Metals

View full text Add to dashboard Cite

show abstract

“…7 is acylated by isobutyryl chloride (8) in carbon disulfide or nitrobenzene as solvent, and the resulting 9 isobutyryl derivative is reduced with NaBH 4 to alcohol 10. Boiling 10 with concentrated HBr the two methyl-groups are removed by hydrolysis, the OH-group is eliminated and the intermediate resorcinol derivative 11 is cyclized in the strongly acid medium, yielding the desired product 1.…”

Section: Choice Of the Synthesis Routementioning

confidence: 99%

“…The direct C-acylation of phenol and naphthol derivatives has been reported for the preparation of 2-hydroxyphenyl or 2-hydroxynaphthyl ketone derivatives [7,8], but the acylation of diphenols is much less documented. In the Friedel-Crafts ring acylation of diphenols with acid chlorides as commonly used acylating agents the classical Lewis acid catalysts are complexed by the phenol and then required in more than equimolar amount.…”

Section: Acylation By Heterogeneous Catalysismentioning

confidence: 99%

An Environmentally Friendly Route for the Synthesis of Benzofurane Derivatives using Selective Ring Acylation of Resorcinol

Békássy¹,

Ágai²,

Farkas³

et al. 2007

Catal Lett

View full text Add to dashboard Cite

International audienceThe synthesis of 2,2-dimethyl-2,3-dihydrobenzofuran- 6-ol, an important intermediate for benzofurane derivatives having pharmaceutical activity, is achieved by an environmentally friendly pathway. Whereas the current synthesis method, based on resorcinol dimethylether, uses or produces harmful, corrosive and dangerous reagents/materials, the procedure proposed here achieves 60% preparative yield for the selective direct ring acylation of resorcinol with isobutyryl chloride, using a solvent-free reaction catalysed by solid acids

show abstract

“…The replacement of homogeneous catalysts by heterogeneous ones in acylation reactions is rather challenging. The most frequently used heterogeneous catalysts for acylation reactions are zeolites [13][14][15][16][17], mesoporous molecular sieves [18][19][20], clays [7,14], sulfated zirconia [14,21,22], heteropoly acids [14,23,24] and Nafion [14,25]. K10-montmorillonite was active and stable catalyst for acylation of ferrocene but the reaction needed reaction temperature as high as 150°C and reaction time of 24 h [7].…”

Section: Introductionmentioning

confidence: 99%

Acylation of Ferrocene with Adamantoyl Chloride and Cinnamoyl Chloride

2010

View full text Add to dashboard Cite

Liquid phase acylation of ferrocene with adamantoyl and cinnamoyl chloride was studied over different structural types of zeolites. The effect of the zeolite structure and acidity, and the influence of the reaction conditions on the ferrocene conversion and selectivity was investigated. The highest ferrocene conversions were achieved over zeolite Beta with Si/Al ratio 12.5 (cinnamoyl chloride 63.5%, adamantoyl chloride 45.9%). It was observed that with decreasing concentration of active sites in zeolite Beta the ferrocene conversion decreases. In addition, it was found that there is an optimum molar ratio of ferrocene to acylating agent, the ferrocene conversion increased with increasing temperature and amount of catalyst. The most important finding is that acylation of ferrocene with adamantoyl and cinnamoyl chloride leads exclusively to monoacylated products, most probably due to a deactivation of the cyclopentadiene rings after the attachment of the first acyl group.

show abstract

Zeolite Catalyzed Aromatic Acylation and Related Reaches

Cited by 73 publications

References 14 publications

Catalytic Reactions over Halide Cluster Complexes of Group 5–7 Metals

Catalytic Reactions over Halide Cluster Complexes of Group 5–7 Metals

An Environmentally Friendly Route for the Synthesis of Benzofurane Derivatives using Selective Ring Acylation of Resorcinol

Acylation of Ferrocene with Adamantoyl Chloride and Cinnamoyl Chloride

Contact Info

Product

Resources

About