Effect of the catalyst nature and quantity on catalytic olefination

Шастин, А. В.; Музалевский, В. M.; Korotchenko, V. N.; Баленкова, Е. С.; Nenaidenko, V. G.

doi:10.1134/s1070428002120047

Cited by 5 publications

(2 citation statements)

References 12 publications

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“…The study of the reaction mechanism of the catalytic olefination reaction showed that the reaction starts with the oxidation of copper (I) chloride with a polyhaloalkane in the presence of a nitrogen-containing ligand to form a complex of copper (II) chloride and a polyhalogenated alkyl radical. The regeneration of copper (I) proceeds under the action of either hydrazone or the addition of products of polyhaloalkyl radicals to hydrazone [73]. Thus, the PHA-nitrogen base-CuCl system works as an oxidizing agent.…”

Section: Resultsmentioning

confidence: 99%

CCl4-TMEDA-CuCl—A Novel Convenient Catalytic System for Dimerization of Terminal Acetylenes in Mild Conditions

Muzalevskiy,

Shastin,

Tirkasheva

et al. 2023

Catalysts

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A novel catalytic system for homocoupling terminal acetylenes was elaborated based on CuCl as a catalyst (10 mol%), TMEDA as a base and CCl4 as an oxidant. The influence of the solvent, base, amount of catalyst and CCl4 on the reaction was investigated. Methanol was found to be the solvent of choice. The broad synthetic scope of the reaction was demonstrated. Diynes with various substituents were prepared in up to 92% yields. The possible reaction mechanism is discussed.

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Section: Resultsmentioning

confidence: 99%

CCl4-TMEDA-CuCl—A Novel Convenient Catalytic System for Dimerization of Terminal Acetylenes in Mild Conditions

Muzalevskiy,

Shastin,

Tirkasheva

et al. 2023

Catalysts

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“…Two mechanistic schemes were proposed for catalytic olefination reaction. Accordingly to the first one, the reaction is initiated by Cu II as a catalyst formed by oxidation of CuCl with polyhalogenated alkane (PHA). Cu II oxidizes hydrazone 478 to give diazoakane 483 , which gives copper-carbene complex 484 after copper-catalyzed extrusion of nitrogen.…”

Section: Chemical Properties Of Polyfluorinated Ethanesmentioning

confidence: 99%

Polyfluorinated Ethanes as Versatile Fluorinated C2-Building Blocks for Organic Synthesis

2015

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CBr₄: A Useful and Efficient Catalyst for One‐Pot Synthesis of 4‐Substituted‐1,4,5,6,7,8‐Hexahydroquinolin‐5‐ones Via Hantzsch Reaction

Wang

Sun

2007

Chin. J. Chem.

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Effect of the catalyst nature and quantity on catalytic olefination

Cited by 5 publications

References 12 publications

CCl4-TMEDA-CuCl—A Novel Convenient Catalytic System for Dimerization of Terminal Acetylenes in Mild Conditions

CCl4-TMEDA-CuCl—A Novel Convenient Catalytic System for Dimerization of Terminal Acetylenes in Mild Conditions

Polyfluorinated Ethanes as Versatile Fluorinated C2-Building Blocks for Organic Synthesis

CBr₄: A Useful and Efficient Catalyst for One‐Pot Synthesis of 4‐Substituted‐1,4,5,6,7,8‐Hexahydroquinolin‐5‐ones Via Hantzsch Reaction

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Effect of the catalyst nature and quantity on catalytic olefination

Cited by 5 publications

References 12 publications

CCl4-TMEDA-CuCl—A Novel Convenient Catalytic System for Dimerization of Terminal Acetylenes in Mild Conditions

CCl4-TMEDA-CuCl—A Novel Convenient Catalytic System for Dimerization of Terminal Acetylenes in Mild Conditions

Polyfluorinated Ethanes as Versatile Fluorinated C2-Building Blocks for Organic Synthesis

CBr4: A Useful and Efficient Catalyst for One‐Pot Synthesis of 4‐Substituted‐1,4,5,6,7,8‐Hexahydroquinolin‐5‐ones Via Hantzsch Reaction

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CBr₄: A Useful and Efficient Catalyst for One‐Pot Synthesis of 4‐Substituted‐1,4,5,6,7,8‐Hexahydroquinolin‐5‐ones Via Hantzsch Reaction