An efficient method for aromatic Friedel–Crafts alkylation, acylation, benzoylation, and sulfonylation reactions

Singh, Ravi P.; Kamble, Rajesh M.; Chandra, Kusum L.; Saravanan, P.; Singh, Vinod K.

doi:10.1016/s0040-4020(00)01005-x

Cited by 91 publications

(29 citation statements)

References 26 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Due to increased environmental concerns, the search for ''green'' catalysts for the FC reaction has assumed new importance. While TfOH itself has been shown to be an active catalyst for the FC reaction, [42] Group XIII metal, [43] hafnium, [43e,43f,43h,44] tin(), [43e] copper(), [45] antimony(), [43i] chlorotitanium, [46] rare-earth [47] and bismuth() triflates [48] have also been reported as active catalysts for FC reactions.…”

Section: Friedel؊crafts Reactionsmentioning

confidence: 99%

Bismuth(III) Triflate in Organic Synthesis

2004

View full text Add to dashboard Cite

show abstract

Section: Friedel؊crafts Reactionsmentioning

confidence: 99%

Bismuth(III) Triflate in Organic Synthesis

2004

View full text Add to dashboard Cite

show abstract

“…The sulfonylation products were characterized by comparison of their spectral (IR, 1 H-NMR), TLC and physical data with authentic samples [20]. Infrared spectra were run on a Shimadzu Model 8700 Fourier transform spectrophotometer.…”

Section: Methodsmentioning

confidence: 99%

“…The sulfonamide partial structure appears to belong to the so-called ''privileged structures'' in medicinal chemistry, and showed several pharmacokinetic properties including metabolic stability. Moreover, 3,4-diaryl and aryl/alkyl sulfones could be synthesized by conventional Friedel-Crafts type sulfonylation of aromatic compounds by sulfonyl halides in the presence of Lewis acids such as AlCl 3 , BF 3 , triflic acid/BiCl 3 , Zn-exchanged zeolites, Fe(III)-exchanged montmorillonite clay, scandium and lanthanide(III) salts [8], and Cu(OTf) 2 or Sn(OTf) 2 [9]. The other branch of organosulfones are sulfonamides which were used widely in pharmaceutical compounds because of their wide range of biological activities such as anticancer, anti-inflammatory and antiviral functions.…”

Section: Introductionmentioning

confidence: 99%

A Simple and Effective Methodology for the Sulfonylation of Alcohols and Aniline under Solvent Free Condition at Room Temperature

Tayebee¹

2012

AJMMS

View full text Add to dashboard Cite

Sulfonylation is an important reaction in the synthesis of naturally occurring bioactive molecules and is one of the most important methods for the protection of alcohols and amines. However, many efforts have been made towards the development of novel methods for the preparation of the target compounds. Most of these methods are involved the reaction of amine and alcohol compounds with sulfonyl chlorides by using an organic solvent, a base, and under high temperatures. Herein, we introduce our findings on the sulfonylation of aniline, 4-nitroaniline, and some alcohols bearing electron donating or withdrawing substituents with p-toluenesulfonyl chloride under very simple conditions in the absence of any expensive additive, as catalyst, and under solvent free condition at room temperature.

show abstract

“…In regards to the synthesis of p-and o-HBP (or other substituted benzophenones) or benzyl benzoates via c-or o-benzoylation, respectively, papers in the literature describe the use of benzoyl chloride or benzyl trichloride also with various homogeneous catalysts: AlCl3 for phenol (and phenol derivatives containing 2,2,6,6,-tetramethylpiperidine) [95], Cu(OTf)2 and Sn(OTf)2 for anisole and veratrole [96,97], Bi(III) salts for phenol [98] and Hf(OTf)4 for phenol [99], even with carboxylic acids [100].…”

Section: Introductionmentioning

confidence: 99%

Zeolite Catalysts for Phenol Benzoylation with Benzoic Acid: Exploring the Synthesis of Hydroxybenzophenones

et al. 2015

View full text Add to dashboard Cite

Abstract:In this paper, we report on the reaction of phenol benzoylation with benzoic acid, which was carried out in the absence of solvent. The aim of this reaction is the synthesis of hydroxybenzophenones, which are important intermediates for the chemical industry. H-beta zeolites offered superior performance compared to H-Y, with a remarkably high conversion of phenol and high yields to the desired compounds, when using a stoichiometric amount of benzoic acid. It was found that the reaction mechanism did not include the intramolecular Fries rearrangement of the primary product phenyl benzoate, but indeed, the bimolecular reaction between phenyl benzoate and phenol mainly contributed to the formation of hydroxybenzophenones. The product distribution was greatly affected by the presence of Lewis-type acid sites in H-beta; it was suggested that the interaction between the aromatic ring and the electrophilic Al 3+ species led to the preferred formation of o-hydroxybenzophenone, because of the decreased charge density on the C atom at the para position of the phenolic ring. H-Y zeolites were efficient than H-beta in phenyl benzoate transformation into hydroxybenzophenones.

show abstract

An efficient method for aromatic Friedel–Crafts alkylation, acylation, benzoylation, and sulfonylation reactions

Cited by 91 publications

References 26 publications

Bismuth(III) Triflate in Organic Synthesis

Bismuth(III) Triflate in Organic Synthesis

A Simple and Effective Methodology for the Sulfonylation of Alcohols and Aniline under Solvent Free Condition at Room Temperature

Zeolite Catalysts for Phenol Benzoylation with Benzoic Acid: Exploring the Synthesis of Hydroxybenzophenones

Contact Info

Product

Resources

About