Efficient direct ester condensation between equimolar amounts of carboxylic acids and alcohols catalyzed by trifluoromethanesulfonic acid (TfOH) in Solkane365mfc

Xu, Xiu‐Hua; Azuma, Ayaka; Taniguchi, Misaki; Tokunaga, Etsuko; Shibata, Norio

doi:10.1039/c3ra00132f

Cited by 7 publications

(4 citation statements)

References 83 publications

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“…The unique properties of TfOH make it a more active catalyst than sulfonic acid; thus, 0.2 mol % of TfOH is sufficient for the excellent conversion of the reactants to 88 (Scheme 10a). This condition is also suitable for the O-acylation of TfOH as an efficient catalyst in the esterification reaction was also studied by Shibata et al [60]. Reactions between various benzoic acid derivatives (86) and octan-1-ol (87) were carried out using a catalytic amount of TfOH in 1,1,1,3,3-pentafluorobutane as a solvent.…”

Section: General Features Of the Tfoh Catalytic Systems For O-acylationmentioning

confidence: 96%

“…Thus, the TfOH catalytic system enables high production yields of 85 at low temperature [59]. TfOH as an efficient catalyst in the esterification reaction was also studied by Shibata et al [60]. Reactions between various benzoic acid derivatives (86) and octan-1-ol (87) were carried out using a catalytic amount of TfOH in 1,1,1,3,3-pentafluorobutane as a solvent.…”

Section: General Features Of the Tfoh Catalytic Systems For O-acylationmentioning

confidence: 99%

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Trifluoromethanesulfonic Acid as Acylation Catalyst: Special Feature for C- and/or O-Acylation Reactions

et al. 2017

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Trifluoromethanesulfonic acid (TfOH) is one of the superior catalysts for acylation. The catalytic activity of TfOH in C-and/or O-acylation has broadened the use of various substrates under mild and neat or forced conditions. In this review, the salient catalytic features of TfOH are summarized, and the unique controllability of its catalytic activity in the tendency of C-acylation and/or O-acylation is discussed.

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Section: General Features Of the Tfoh Catalytic Systems For O-acylationmentioning

confidence: 96%

Section: General Features Of the Tfoh Catalytic Systems For O-acylationmentioning

confidence: 99%

Trifluoromethanesulfonic Acid as Acylation Catalyst: Special Feature for C- and/or O-Acylation Reactions

et al. 2017

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“…TFEO-Pc also shows high solubility in Solkane ® 365 mfc, which is a type of fluorine-based solvent. Solkane ® 365 mfc is a proven candidate solvent that does not deplete ozone, allowing the use of Solkane ® 365 mfc as an alternative to organic solvents to reduce the environmental burden [ 61 – 62 ]. An unsymmetrical type of TFEO-ZnPc with ethynyl group ( 4 ) shows high solubility in Solkane ® 365 mfc while a Glaser-type coupling reaction catalyzed by copper with Solkane ® 365 mfc as the medium have been reported ( Scheme 2 ) [ 63 ].…”

Section: Reviewmentioning

confidence: 99%

Synthesis and application of trifluoroethoxy-substituted phthalocyanines and subphthalocyanines

Mori

Shibata

2017

Beilstein J. Org. Chem.

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Phthalocyanines and subphthalocyanines are attracting attention as functional dyes that are applicable to organic solar cells, photodynamic therapy, organic electronic devices, and other applications. However, phthalocyanines are generally difficult to handle due to their strong ability to aggregate, so this property must be controlled for further applications of phthalocyanines. On the other hand, trifluoroethoxy-substituted phthalocyanines are known to suppress aggregation due to repulsion of the trifluoroethoxy group. Furthermore, the electronic characteristics of phthalocyanines are significantly changed by the strong electronegativity of fluorine. Therefore, it is expected that trifluoroethoxy-substituted phthalocyanines can be applied to new industrial fields. This review summarizes the synthesis and application of trifluoroethoxy-substituted phthalocyanine and subphthalocyanine derivatives.

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“…Although mesoporous sulfonic acid esterification catalysts are reported, they are still in the development stage in terms of amount of catalyst and alcohol used. Reports of direct batchwise Fischer–Speier esterification using acid-catalyst concentrations below 1 mol % are extremely rare . For example, a homogeneous hafnium salt catalyst and a fluorinated solvent system has been developed.…”

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confidence: 99%

Second-Generation meta-Phenolsulfonic Acid–Formaldehyde Resin as a Catalyst for Continuous-Flow Esterification

Ota

Baek

et al. 2019

Org. Lett.

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A second-generation m-phenolsulfonic acid−formaldehyde resin (PAFR II) catalyst was prepared by condensation polymerization of sodium m-phenolsulfonate and paraformaldehyde in an aqueous H 2 SO 4 solution. This reusable, robust acid resin catalyst was improved in both catalytic activity and stability, maintaining the characteristics of the previous generation catalyst (p-phenolsulfonic acid−formaldehyde resin). PAFR II was applied in the batchwise and continuous-flow direct esterification without water removal and provided higher product yields in continuousflow esterification than any other commercial ion-exchanged acid catalyst tested.

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Efficient direct ester condensation between equimolar amounts of carboxylic acids and alcohols catalyzed by trifluoromethanesulfonic acid (TfOH) in Solkane365mfc

Cited by 7 publications

References 83 publications

Trifluoromethanesulfonic Acid as Acylation Catalyst: Special Feature for C- and/or O-Acylation Reactions

Trifluoromethanesulfonic Acid as Acylation Catalyst: Special Feature for C- and/or O-Acylation Reactions

Synthesis and application of trifluoroethoxy-substituted phthalocyanines and subphthalocyanines

Second-Generation meta-Phenolsulfonic Acid–Formaldehyde Resin as a Catalyst for Continuous-Flow Esterification

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