Protic Ionic Liquid as Reagent, Catalyst, and Solvent: 1-Methylimidazolium Thiocyanate
Ivan A. Andreev,Nina K. Ratmanova,André U. Augustin,Olga A. Ivanova,Olga A. Ivanova,Irina I. Levina,Victor N. Khrustalev,Daniel B. Werz,Igor V. Trushkov +8 more
TLDR
In this article, the authors proposed a triple role of protic ionic liquids with nucleophilic anions: a regenerable solvent, a Bronsted acid inducing diverse transformations via general acid catalysis and a source of a nucleophile.Abstract:
We propose a new concept of the triple role of protic ionic liquids with nucleophilic anions: a) a regenerable solvent, b) a Bronsted 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.read more
Citations
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Diverse Applications of Ionic Liquids: A Comprehensive Review
TL;DR: The vast utilization and scope of ionic liquids in a variety of fields have been presented based upon available literature as mentioned in this paper , and a systematic and concise analysis of the various ionic liquid applications has been done highlighting some recent significant advances in every zone.
Journal ArticleDOI
Exploiting Heavier Organochalcogen Compounds in Donor-Acceptor Cyclopropane Chemistry.
André U. Augustin,Daniel B. Werz +1 more
TL;DR: The use of these highly strained three-membered entities paved the way to innovative and origi... as mentioned in this paper, and the use of cyclopropanes has gained increased momentum over the past two decades.
Journal ArticleDOI
Cycloadditions of Donor-Acceptor Cyclopropanes and -butanes using S=N-Containing Reagents: Access to Cyclic Sulfinamides, Sulfonamides, and Sulfinamidines
Gwyndaf A. Oliver,Maximilian N. Loch,André U. Augustin,Pit Steinbach,Mohammed Sharique,Uttam K. Tambar,Peter G. Jones,Christoph Bannwarth,Daniel B. Werz +8 more
TL;DR: In this paper, the (3+2)-and (4+2) cycloadditions of D-A cyclopropanes and cyclobutanes with N-sulfinylamines and a sulfur diimide were presented.
Journal ArticleDOI
Expanding Stereoelectronic Limits of endo-tet Cyclizations: Synthesis of Benz[b]azepines from Donor-Acceptor Cyclopropanes.
Anna E. Vartanova,Andrey Yu Plodukhin,Nina K. Ratmanova,Ivan A. Andreev,Mikhail N Anisimov,Nikita Gudimchuk,Victor B. Rybakov,Irina I. Levina,Olga A. Ivanova,Olga A. Ivanova,Igor V. Trushkov,Igor V. Alabugin +11 more
TL;DR: In this paper, it was shown that donor-acceptor cyclopropanes can provide a seven-membered ring via a genuine 6-endometrized cyclization process.
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A Review on Ionic Liquids-Based Membranes for Middle and High Temperature Polymer Electrolyte Membrane Fuel Cells (PEM FCs)
TL;DR: In this article, the use of polymer electrolyte membranes (PEMs) possessing ionic liquids (ILs) in middle and high temperature PEM fuel cells (MT-PEMFCs) has been increased.
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