BF3·OEt2: An Efficient Catalyst for Transesterification of β-Ketoesters

Yang, Jinhui; Ji, Cong‐Bin; Yan-min, Zhao; Li, Yunfeng; Jiang, Shizhi; Zhang, Zhiwei; Ji, Yongqiang; Liu, Wanyi

doi:10.1080/00397910903029842

Cited by 20 publications

(10 citation statements)

References 18 publications

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“…The residue was concentrated and purified by column chromatography using hexane and ethyl acetate as eluents. The spectroscopic characterization of all the compounds matches well with the literature . (see supporting information).…”

Section: Methodssupporting

confidence: 78%

“…When the parent carboxylic acids are labile and difficult to isolate then transesterification becomes more advantageous . Among the esters, β ‐keto esters are of special interest because of their electrophilic and nucleophlic centers, making them a valuable synthon for the synthesis of natural products such as karrikinolide (KAR1), tetrahydrozerumbone, serricornine and trichodiene …”

Section: Introductionmentioning

confidence: 99%

“…Again, NaBH 4 is a common reducing reagent and alcoholic solutions of sodium borohydride are neither strongly acidic nor basic, which makes it suitable for transesterification of acid‐ and base‐labile esters . Several Lewis acid catalysts such as BF 3 .OEt 2 , BiCl 3 and Bi(NO 3 ) 5 have also been reported for the transesterification of β ‐keto esters with alcohol.…”

Section: Introductionmentioning

confidence: 99%

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AgOTf‐catalyzed transesterification of β‐keto esters

Das

Chakraborty

2012

Applied Organom Chemis

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Section: Methodssupporting

confidence: 78%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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AgOTf‐catalyzed transesterification of β‐keto esters

Das

Chakraborty

2012

Applied Organom Chemis

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“…The alkylation process has gained popularity and is being applied in laboratories and in some cases in industry. While reports of the esterification of carboxylic acids catalysed by BTE are known and take place in the presence of an alcohol [19][20][21], the alkylation of carboxylic acids by an ethyl moiety of BTE in the absence of ethyl alcohol from the reaction system is unexpected and to the best of our knowledge has not been reported and therefore forms the basis of this communication.…”

Section: Introductionmentioning

confidence: 93%

Unprecedented alkylation of carboxylic acids by boron trifluoride etherate

Jumbam¹,

Maganga²,

Masamba³

et al. 2018

Bull. Chem. Soc. Eth.

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The alkylation of carboxylic acids by an ethyl moiety of boron trifluoride etherate in the absence of ethyl alcohol from the reaction system is unexpected and novel. Both aromatic and aliphatic carboxylic acids were clearly alkylated affording good yields in short reaction times with the exception of nicotinic acid that necessitated an overnight reaction. It was noted that while ortho-substituted hydroxyl groups of carboxylic acids investigated were not affected by alkylation, those of meta-and para-substituted carboxylic acids were partially etherified. Furthermore, the alkylation reaction was found to be compatible with a range of functional groups such as halogens, amino and nitro groups except for the alkene function of undecylenic acid that underwent polymerisation with concomitant alkylation of its carboxylic acid function.

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“…Thus, an efficient, economical and environmentally benign commercially available or new catalyst is highly desirable for this procedure. In continuation of our work with regard to the preparation of new catalyst for various organic transformations, [ 79 , 80 , 81 ] we herein report a strategy in which commercially available boron trifluoride diethyl etherfunctions as an effective catalyst [ 82 , 83 ] for the synthesis of indolylsuccinimides ( Scheme 1 ). Interestingly, unlike earlier procedures, it offers a convenient single step reaction and works well with the electron-deficient indoles under mild reaction conditions.…”

Section: Introductionmentioning

confidence: 99%

BF3-OEt2 Catalyzed C3-Alkylation of Indole: Synthesis of Indolylsuccinimidesand Their Cytotoxicity Studies

Shaikh¹,

Rahim²,

Faazil³

et al. 2021

Molecules

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A simple and efficient BF3-OEt2 promoted C3-alkylation of indole has been developed to obtain3-indolylsuccinimidesfrom commercially available indoles and maleimides, with excellent yields under mild reaction conditions. Furthermore, anti-proliferative activity of these conjugates was evaluated against HT-29 (Colorectal), Hepg2 (Liver) and A549 (Lung) human cancer cell lines. One of the compounds, 3w, having N,N-Dimethylatedindolylsuccinimide is a potent congener amongst the series with IC50 value 0.02 µM and 0.8 µM against HT-29 and Hepg2 cell lines, respectively, and compound 3i was most active amongst the series with IC50 value 1.5 µM against A549 cells. Molecular docking study and mechanism of reaction have briefly beendiscussed. This method is better than previous reports in view of yield and substrate scope including electron deficient indoles.

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BF₃·OEt₂: An Efficient Catalyst for Transesterification of β-Ketoesters

Cited by 20 publications

References 18 publications

AgOTf‐catalyzed transesterification of β‐keto esters

AgOTf‐catalyzed transesterification of β‐keto esters

Unprecedented alkylation of carboxylic acids by boron trifluoride etherate

BF3-OEt2 Catalyzed C3-Alkylation of Indole: Synthesis of Indolylsuccinimidesand Their Cytotoxicity Studies

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