Synthesis of heterocycles from allenes containing electron-withdrawing substituents under the conditions of electrophilic activation: recent advances

A straightforward, user-friendly, efficient protocol for the one pot, ZnI 2 -catalyzed allenylation of terminal alkynes with pyrrolidine and ketones, toward trisubstituted allenes, is described. Trisubstituted allenes can be obtained under either conventional heating or microwave irradiation conditions, which significantly reduces the reaction time. A sustainable, widely available, and low-cost metal salt catalyst is employed, and the reactions are carried out under solvent-free conditions. Among others, synthetically valuable allenes bearing functionalities such as amide, hydroxyl, or phthalimide can be efficiently prepared. Mechanistic experiments, including kinetic isotope effect measurements and density functional theory (DFT) calculations, suggest a rate-determining [1,5]-hydride transfer during the transformation of the intermediate propargylamine to the final allene.

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Diastereoselective cycloaddition of tosylpropadiene to azomethine ylides, derived from proline and carbonyl compounds: an experimental and DFT study

Stepakov

Filatov

Бойцов

et al. 2021

Phosphorus, Sulfur, and Silicon and the Related Elements

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Synthesis of heterocycles from allenes containing electron-withdrawing substituents under the conditions of electrophilic activation: recent advances

Cited by 3 publications

References 26 publications

Synthesis of 2-(5H)-furanones by cyclization of alkyl allene carboxylates in triflic acid

Synthesis of 2-(5H)-furanones by cyclization of alkyl allene carboxylates in triflic acid

Zinc Iodide Catalyzed Synthesis of Trisubstituted Allenes from Terminal Alkynes and Ketones

Diastereoselective cycloaddition of tosylpropadiene to azomethine ylides, derived from proline and carbonyl compounds: an experimental and DFT study

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