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Protic Ionic Liquid as Reagent, Catalyst, and Solvent: 1‐Methylimidazolium Thiocyanate Full article

Journal Angewandte Chemie International Edition
ISSN: 1433-7851 , E-ISSN: 1521-3773
Output data Year: 2021, Volume: 60, Number: 14, Pages: 7927-7934 Pages count : 8 DOI: 10.1002/anie.202016593
Authors Andreev Ivan A. 1,2,3 , Ratmanova Nina K. 1,3 , Augustin André U. 4 , Ivanova Olga A. 5,2 , Levina Irina I. 6 , Khrustalev Victor N. 7,2 , Werz Daniel B. 4 , Trushkov Igor V. 1,2
Affiliations
1 Dmitry Rogachev National Medical Research Center of Pediatric Hematology, Oncology and Immunology, Samory Mashela 1, 117997 Moscow, Russian Federation
2 N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky pr. 47, 119991 Moscow, Russian Federation
3 These authors contributed equally to this work.
4 Technische Universität Braunschweig Institute of Organic Chemistry Hagenring 30 38106 Braunschweig Germany
5 Department of Chemistry Lomonosov Moscow State University Leninskie Gory 1–3 119991 Moscow Russian Federation
6 Institute of Biochemical Physics, Russian Academy of Sciences, Kosygina 4, 119334 Moscow, Russian Federation
7 Faculty of Science, RUDN University, Miklukho-Maklaya 6, 117198 Moscow, Russian Federation

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.
Cite: Andreev I.A. , Ratmanova N.K. , Augustin A.U. , Ivanova O.A. , Levina I.I. , Khrustalev V.N. , Werz D.B. , Trushkov I.V.
Protic Ionic Liquid as Reagent, Catalyst, and Solvent: 1‐Methylimidazolium Thiocyanate
Angewandte Chemie International Edition. 2021. V.60. N14. P.7927-7934. DOI: 10.1002/anie.202016593 WOS Scopus OpenAlex
Identifiers:
Web of science: WOS:000621806900001
Scopus: 2-s2.0-85101701983
OpenAlex: W3118482656
Citing:
DB Citing
OpenAlex 77
Web of science 65
Scopus 71
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