Base-free benzylation of 1,3-dicarbonyl compounds using sulfamic acid supported on silica by linker: a combined experimental and theoretical approach

Karimzadeh, Morteza; Asl, Hamed Saberi; Hashemi, Hajar; Saberi, Dariush; Niknam, Khodabakhsh

doi:10.1007/s00706-018-2284-x

Cited by 4 publications

(3 citation statements)

References 55 publications

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“…Recently, silica-bonded N-propyl sulfamic acid (SBNPSA) was further employed for direct benzylation of 1,3-dicarbonyl compounds by secondary aromatic alcohols or styrenes. [128] The investigation revealed that nitromethane was the best solvent under reflux conditions (Scheme 68). The generality of the method was investigated by the benzylation of 1,3-diketones with various aromatic alcohols and styrenes, where high yields (85-97 %) of the corresponding compounds were obtained in 15-20 min.…”

Section: Sa Supported On Silica Coated Functionalized Magnetic Fe 3 O 4 Nanoparticlesmentioning

confidence: 99%

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Sulfamic Acid as Versatile Green Catalyst Used For Synthetic Organic Chemistry: A Comprehensive Update

Chopra

Lambat²,

Mahmood

et al. 2021

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In recent times, synthetic organic reactions have gained significant attention as they are becoming a versatile tool in the synthesis of pharmaceuticals, agrochemicals and their intermediates. Sulfamic acid (SA) is an acid catalyst that demonstrated high efficiency in various organic transformations that will be highlighted in this review. These include efforts to develop green approaches using SA catalyst for the CÀ C bond formation reactions and functional group trans-formations, as well as the synthesis of various OÀ and Nheterocyclic compounds and other miscellaneous reactions including multicomponent reactions. The easy recovery (for subsequent reuse) of the catalyst by filtration without the need for solvents is an important advantage of SA catalyst. In this review, SA promoted greener methodologies that were developed and the applicability of these methodologies are addressed.

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Section: Sa Supported On Silica Coated Functionalized Magnetic Fe 3 O 4 Nanoparticlesmentioning

confidence: 99%

“…Recently, silica‐bonded N ‐propyl sulfamic acid (SBNPSA) was further employed for direct benzylation of 1,3‐dicarbonyl compounds by secondary aromatic alcohols or styrenes [128] . The investigation revealed that nitromethane was the best solvent under reflux conditions (Scheme 68).…”

Section: Synthesis Using Modified Sa As Heterogeneous Catalystmentioning

confidence: 99%

Sulfamic Acid as Versatile Green Catalyst Used For Synthetic Organic Chemistry: A Comprehensive Update

Chopra

Lambat²,

Mahmood

et al. 2021

ChemistrySelect

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“…The benzylation of 1,3‐dicarbonyl compounds is one of the useful methods to construct the C−C bond in organic synthesis, [1] which have an important value in applications to generate many bioactive structural motifs [2] . For example, reglitazar, [3] as an insulin‐sensitizing agent, as well as tipranavir, [2] one of the HIV‐1 protease inhibitors, both involved this motif. Although the poor reactivity of alcohol hydroxyl toward nucleophilic reagents, [4] the requirement is a limitation [5] .…”

Section: Introductionmentioning

confidence: 99%

Benzylation of 1,3‐Dicarbonyl Compounds with Benzyl Alcohols Promoted by Perfluorosulfonic Acid Resin

Zhang,

Yang,

Pei

et al. 2023

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The catalytic performance of Perfluorosulfonic acid resin (PFSA), a solid superacid, was studied in the catalytic benzylation of 1,3‐dicarbonyl compounds with benzylic alcohols. The PFSA‐catalyzed reactions could proceed smoothly to provide the products under solvent‐free conditions or in toluene and dichloromethane, which gave moderate to excellent yields. Due to its high chemical stability, PFSA was quite stable under the reaction conditions and could be recovered at least eight times without significant reduction of its catalytic effect. Moreover, this reaction was investigated at a 20 mmol scale, which indicated the potential applicability of the large‐scale industrial synthesis. Finally, the mechanism of the PFSA‐catalyzed benzylation of 1,3‐dicarbonyl compounds with benzylic alcohols was also investigated.

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Diastereoconvergent Dehydrative Nucleophilic Substitutions of Diastereomeric Diarylmethanols with 1,3‐Dicarbonyls Catalyzed by SnBr₄

2019

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Base-free benzylation of 1,3-dicarbonyl compounds using sulfamic acid supported on silica by linker: a combined experimental and theoretical approach

Cited by 4 publications

References 55 publications

Sulfamic Acid as Versatile Green Catalyst Used For Synthetic Organic Chemistry: A Comprehensive Update

Sulfamic Acid as Versatile Green Catalyst Used For Synthetic Organic Chemistry: A Comprehensive Update

Benzylation of 1,3‐Dicarbonyl Compounds with Benzyl Alcohols Promoted by Perfluorosulfonic Acid Resin

Diastereoconvergent Dehydrative Nucleophilic Substitutions of Diastereomeric Diarylmethanols with 1,3‐Dicarbonyls Catalyzed by SnBr₄

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Base-free benzylation of 1,3-dicarbonyl compounds using sulfamic acid supported on silica by linker: a combined experimental and theoretical approach

Cited by 4 publications

References 55 publications

Sulfamic Acid as Versatile Green Catalyst Used For Synthetic Organic Chemistry: A Comprehensive Update

Sulfamic Acid as Versatile Green Catalyst Used For Synthetic Organic Chemistry: A Comprehensive Update

Benzylation of 1,3‐Dicarbonyl Compounds with Benzyl Alcohols Promoted by Perfluorosulfonic Acid Resin

Diastereoconvergent Dehydrative Nucleophilic Substitutions of Diastereomeric Diarylmethanols with 1,3‐Dicarbonyls Catalyzed by SnBr4

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Diastereoconvergent Dehydrative Nucleophilic Substitutions of Diastereomeric Diarylmethanols with 1,3‐Dicarbonyls Catalyzed by SnBr₄