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Henri Doucet - One of the best experts on this subject based on the ideXlab platform.
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Palladium-Based Catalytic System for the Direct C3-Arylation of Furan-2-carboxamides and Thiophene-2-carboxamides
ChemCatChem, 2012Co-Authors: Karima Si larbi, Nouria Laidaoui, Kassem Beydoun, Abdellah Miloudi, Safia Djabbar, Douniazad El abed, Henri DoucetAbstract:The palladium-catalyzed direct arylation of Furans or thiophenes that contained secondary carboxamides at the C2 position proceeded regioselectively at either the C3 or C5 positions, depending on the reaction conditions. The nature of the base was crucial for controlling the regioselectivity of the reaction. We had previously observed that, in the presence of potassium acetate, direct arylation at the C5 position was favored. Herein, we report that the use of cesium carbonate as the base and xylene as the solvent selectively afforded the C3-arylated Furans or thiophenes. The reactivity of furan-2-carboxamides and thiophene-2-carboxamides were similar. The reaction tolerated a range of functional groups on the aryl bromide and also heteroaryl bromide substrates.
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Palladium‐Based Catalytic System for the Direct C3‐Arylation of Furan‐2‐carboxamides and Thiophene‐2‐carboxamides
ChemCatChem, 2012Co-Authors: Karima Si Larbi, Nouria Laidaoui, Kassem Beydoun, Abdellah Miloudi, Douniazad El Abed, Safia Djabbar, Henri DoucetAbstract:The palladium-catalyzed direct arylation of Furans or thiophenes that contained secondary carboxamides at the C2 position proceeded regioselectively at either the C3 or C5 positions, depending on the reaction conditions. The nature of the base was crucial for controlling the regioselectivity of the reaction. We had previously observed that, in the presence of potassium acetate, direct arylation at the C5 position was favored. Herein, we report that the use of cesium carbonate as the base and xylene as the solvent selectively afforded the C3-arylated Furans or thiophenes. The reactivity of furan-2-carboxamides and thiophene-2-carboxamides were similar. The reaction tolerated a range of functional groups on the aryl bromide and also heteroaryl bromide substrates.
Qiang Tang - One of the best experts on this subject based on the ideXlab platform.
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paal knorr furan synthesis using ticl4 as dehydrating agent a concise furan synthesis from α haloketones and β dicarbonyl compounds
Asian Journal of Organic Chemistry, 2017Co-Authors: Dan Lu, Yi Peng, Qiang TangAbstract:An efficient and facile method for the Paal-Knorr furan synthesis using titanium tetrachloride as dehydrating agent is described. Tri-carbonyl compounds, prepared through the nucleophilic substitution of α-halogenated ketones and β-dicarbonyl compounds, are easily condensed to their corresponding poly-substituted Furans. The reaction also occurs efficiently with tetra-carbonyl compounds derived by dimerization of β-dicarbonyl compounds.
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Paal–Knorr Furan Synthesis Using TiCl4 as Dehydrating Agent: A Concise Furan Synthesis from α‐Haloketones and β‐Dicarbonyl Compounds
Asian Journal of Organic Chemistry, 2017Co-Authors: Dan Lu, Yi Peng, Qiang TangAbstract:An efficient and facile method for the Paal-Knorr furan synthesis using titanium tetrachloride as dehydrating agent is described. Tri-carbonyl compounds, prepared through the nucleophilic substitution of α-halogenated ketones and β-dicarbonyl compounds, are easily condensed to their corresponding poly-substituted Furans. The reaction also occurs efficiently with tetra-carbonyl compounds derived by dimerization of β-dicarbonyl compounds.
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understanding the scope of feist benary furan synthesis chemoselectivity and diastereoselectivity of the reaction between α halo ketones and β dicarbonyl compounds
European Journal of Organic Chemistry, 2016Co-Authors: Yi Peng, Qiang Feng, Qiang TangAbstract:Feist–Benary furan synthesis, the reaction between α-halocarbonyl and β-dicarbonyl compounds, has been known as an efficient method for generating many different types of Furans containing a carbonyl group at C-3. However, it has also been reported that, under similar reaction conditions, intermediate tricarbonyl species could be further converted to alternative furan isomers through the application of a Paal–Knorr synthesis. In this manuscript, we investigate the chemoselectivity and diastereoselectivity of furan synthesis from α-halo ketones and β-dicarbonyl compounds, by carrying out the separation and characterization of the intermediates involved in the reaction. Additionally, a one-pot Feist–Benary furan synthesis from α-halo ketones and β-dicarbonyl compounds without any base or solvent has also been developed.
Yi Peng - One of the best experts on this subject based on the ideXlab platform.
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paal knorr furan synthesis using ticl4 as dehydrating agent a concise furan synthesis from α haloketones and β dicarbonyl compounds
Asian Journal of Organic Chemistry, 2017Co-Authors: Dan Lu, Yi Peng, Qiang TangAbstract:An efficient and facile method for the Paal-Knorr furan synthesis using titanium tetrachloride as dehydrating agent is described. Tri-carbonyl compounds, prepared through the nucleophilic substitution of α-halogenated ketones and β-dicarbonyl compounds, are easily condensed to their corresponding poly-substituted Furans. The reaction also occurs efficiently with tetra-carbonyl compounds derived by dimerization of β-dicarbonyl compounds.
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Paal–Knorr Furan Synthesis Using TiCl4 as Dehydrating Agent: A Concise Furan Synthesis from α‐Haloketones and β‐Dicarbonyl Compounds
Asian Journal of Organic Chemistry, 2017Co-Authors: Dan Lu, Yi Peng, Qiang TangAbstract:An efficient and facile method for the Paal-Knorr furan synthesis using titanium tetrachloride as dehydrating agent is described. Tri-carbonyl compounds, prepared through the nucleophilic substitution of α-halogenated ketones and β-dicarbonyl compounds, are easily condensed to their corresponding poly-substituted Furans. The reaction also occurs efficiently with tetra-carbonyl compounds derived by dimerization of β-dicarbonyl compounds.
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understanding the scope of feist benary furan synthesis chemoselectivity and diastereoselectivity of the reaction between α halo ketones and β dicarbonyl compounds
European Journal of Organic Chemistry, 2016Co-Authors: Yi Peng, Qiang Feng, Qiang TangAbstract:Feist–Benary furan synthesis, the reaction between α-halocarbonyl and β-dicarbonyl compounds, has been known as an efficient method for generating many different types of Furans containing a carbonyl group at C-3. However, it has also been reported that, under similar reaction conditions, intermediate tricarbonyl species could be further converted to alternative furan isomers through the application of a Paal–Knorr synthesis. In this manuscript, we investigate the chemoselectivity and diastereoselectivity of furan synthesis from α-halo ketones and β-dicarbonyl compounds, by carrying out the separation and characterization of the intermediates involved in the reaction. Additionally, a one-pot Feist–Benary furan synthesis from α-halo ketones and β-dicarbonyl compounds without any base or solvent has also been developed.
Safia Djabbar - One of the best experts on this subject based on the ideXlab platform.
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Palladium-Based Catalytic System for the Direct C3-Arylation of Furan-2-carboxamides and Thiophene-2-carboxamides
ChemCatChem, 2012Co-Authors: Karima Si larbi, Nouria Laidaoui, Kassem Beydoun, Abdellah Miloudi, Safia Djabbar, Douniazad El abed, Henri DoucetAbstract:The palladium-catalyzed direct arylation of Furans or thiophenes that contained secondary carboxamides at the C2 position proceeded regioselectively at either the C3 or C5 positions, depending on the reaction conditions. The nature of the base was crucial for controlling the regioselectivity of the reaction. We had previously observed that, in the presence of potassium acetate, direct arylation at the C5 position was favored. Herein, we report that the use of cesium carbonate as the base and xylene as the solvent selectively afforded the C3-arylated Furans or thiophenes. The reactivity of furan-2-carboxamides and thiophene-2-carboxamides were similar. The reaction tolerated a range of functional groups on the aryl bromide and also heteroaryl bromide substrates.
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Palladium‐Based Catalytic System for the Direct C3‐Arylation of Furan‐2‐carboxamides and Thiophene‐2‐carboxamides
ChemCatChem, 2012Co-Authors: Karima Si Larbi, Nouria Laidaoui, Kassem Beydoun, Abdellah Miloudi, Douniazad El Abed, Safia Djabbar, Henri DoucetAbstract:The palladium-catalyzed direct arylation of Furans or thiophenes that contained secondary carboxamides at the C2 position proceeded regioselectively at either the C3 or C5 positions, depending on the reaction conditions. The nature of the base was crucial for controlling the regioselectivity of the reaction. We had previously observed that, in the presence of potassium acetate, direct arylation at the C5 position was favored. Herein, we report that the use of cesium carbonate as the base and xylene as the solvent selectively afforded the C3-arylated Furans or thiophenes. The reactivity of furan-2-carboxamides and thiophene-2-carboxamides were similar. The reaction tolerated a range of functional groups on the aryl bromide and also heteroaryl bromide substrates.
Nouria Laidaoui - One of the best experts on this subject based on the ideXlab platform.
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Palladium-Based Catalytic System for the Direct C3-Arylation of Furan-2-carboxamides and Thiophene-2-carboxamides
ChemCatChem, 2012Co-Authors: Karima Si larbi, Nouria Laidaoui, Kassem Beydoun, Abdellah Miloudi, Safia Djabbar, Douniazad El abed, Henri DoucetAbstract:The palladium-catalyzed direct arylation of Furans or thiophenes that contained secondary carboxamides at the C2 position proceeded regioselectively at either the C3 or C5 positions, depending on the reaction conditions. The nature of the base was crucial for controlling the regioselectivity of the reaction. We had previously observed that, in the presence of potassium acetate, direct arylation at the C5 position was favored. Herein, we report that the use of cesium carbonate as the base and xylene as the solvent selectively afforded the C3-arylated Furans or thiophenes. The reactivity of furan-2-carboxamides and thiophene-2-carboxamides were similar. The reaction tolerated a range of functional groups on the aryl bromide and also heteroaryl bromide substrates.
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Palladium‐Based Catalytic System for the Direct C3‐Arylation of Furan‐2‐carboxamides and Thiophene‐2‐carboxamides
ChemCatChem, 2012Co-Authors: Karima Si Larbi, Nouria Laidaoui, Kassem Beydoun, Abdellah Miloudi, Douniazad El Abed, Safia Djabbar, Henri DoucetAbstract:The palladium-catalyzed direct arylation of Furans or thiophenes that contained secondary carboxamides at the C2 position proceeded regioselectively at either the C3 or C5 positions, depending on the reaction conditions. The nature of the base was crucial for controlling the regioselectivity of the reaction. We had previously observed that, in the presence of potassium acetate, direct arylation at the C5 position was favored. Herein, we report that the use of cesium carbonate as the base and xylene as the solvent selectively afforded the C3-arylated Furans or thiophenes. The reactivity of furan-2-carboxamides and thiophene-2-carboxamides were similar. The reaction tolerated a range of functional groups on the aryl bromide and also heteroaryl bromide substrates.