ArticleAngewandte Chemie (International ed. in English)2021
Protic Ionic Liquid as Reagent, Catalyst, and Solvent: 1-Methylimidazolium Thiocyanate.
Article in Angewandte Chemie (International ed. in English), 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 6 papers.
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Who cites it
6 citing papers in PubMed.
- Ionolysis of flexible polyurethane waste using ionic liquids for efficient and sustainable polyol recovery.Communications chemistry · 2026Article
- Hydroxyl carboxylate anion catalyzed depolymerization of biopolyesters and transformation to chemicals.Chemical science · 2024Article
- Photocascade chemoselective controlling of ambident thio(seleno)cyanates with alkenes via catalyst modulation.Nature communications · 2024Article
- Cycloadditions of Donor-Acceptor Cyclopropanes and -butanes using S=N-Containing Reagents: Access to Cyclic Sulfinamides, Sulfonamides, and Sulfinamidines.Angewandte Chemie (International ed. in English) · 2021Article
- A Review on Ionic Liquids-Based Membranes for Middle and High Temperature Polymer Electrolyte Membrane Fuel Cells (PEM FCs).International journal of molecular sciences · 2021Review
- Protic Ionic Liquid as Reagent, Catalyst, and Solvent: 1-Methylimidazolium Thiocyanate.Angewandte Chemie (International ed. in English) · 2021Article
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Authors and funding
8 authors.
Funding
Abstract
We propose a new concept of the triple role of protic ionic liquids with nucleophilic anions: a) a regenerable solvent, b) a Brønsted acid inducing diverse transformations via general acid catalysis, and c) a source of a nucleophile. The efficiency of this strategy was demonstrated using thiocyanate-based protic ionic liquids for the ring-opening of donor-acceptor cyclopropanes. A wide variety of activated cyclopropanes were found to react with 1-methylimidazolium thiocyanate under mild metal-free conditions via unusual nitrogen attack of the ambident thiocyanate ion on the electrophilic center of the three-membered ring affording pyrrolidine-2-thiones bearing donor and acceptor substituents at the C(5) and C(3) atoms, respectively, in a single time-efficient step. The ability of 1-methylimidazolium thiocyanate to serve as a triplex reagent was exemplarily illustrated by (4+2)-annulation with 1-acyl-2-(2-hydroxyphenyl)cyclopropane, epoxide ring-opening and other organic transformations.
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Registered trials
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