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Imidazolium Based Fluorous N-Heterocyclic Carbenes as Effective and Recyclable Organocatalysts for Redox Esterification
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SYSNO ASEP 0524181 Druh ASEP J - Článek v odborném periodiku Zařazení RIV J - Článek v odborném periodiku Poddruh J Článek ve WOS Název Imidazolium Based Fluorous N-Heterocyclic Carbenes as Effective and Recyclable Organocatalysts for Redox Esterification Tvůrce(i) Červenková Šťastná, Lucie (UCHP-M) RID, ORCID, SAI
Bílková, Veronika (UCHP-M) SAI
Cézová, T. (CZ)
Cuřínová, Petra (UCHP-M) RID, SAI, ORCID
Karban, Jindřich (UCHP-M) RID, ORCID, SAI
Čermák, Jan (UCHP-M) RID, ORCID, SAI
Krupková, Alena (UCHP-M) RID, ORCID, SAI
Strašák, Tomáš (UCHP-M) RID, ORCID, SAIZdroj.dok. European Journal of Organic Chemistry - ISSN 1434-193X
Roč. 2020, č. 24 (2020), s. 3591-3598Poč.str. 9 s. Jazyk dok. eng - angličtina Země vyd. DE - Německo Klíč. slova fluorous ionic liquids ; N-heterocyclic carbenes ; organocatalysis Vědní obor RIV CC - Organická chemie Obor OECD Organic chemistry Způsob publikování Omezený přístup Institucionální podpora UCHP-M - RVO:67985858 UT WOS 000538770500001 EID SCOPUS 85086030389 DOI 10.1002/ejoc.202000273 Anotace A series of new highly fluorophilic ionic liquids ( f > 110) was synthetized from 3‑iodopropyltris(3,3,4,4,5,5,6,6,7,7,8,8,8‐tridecafluorooctyl)silane and N‐alkyl imidazoles, followed by anion exchange. N‐heterocyclic carbenes generated in situ from obtained imidazolium salts were employed to catalyze redox esterification ( umpolung ) of cinnamaldehyde with alcohols. The most effective N‐methyl derivative with iodide as a counter anion was studied in detail with respect to the optimization of reaction conditions, substrate scope and recyclability. Recovery of the precatalyst was achieved using either fluorous extraction or performing the reaction in suitable fluorous biphase system with direct recycling of the fluorinated precatalyst phase. For both tested options, the catalytic activity did not significantly decrease within 5 subsequent cycles. The redox esterification was shown to proceed also in supercritical carbon dioxide (scCO 2 ) as an alternative solvent where the activity of the fluorinated catalyst was also superior to the nonfluorinated model, while retaining the benefit of easy recycling. Pracoviště Ústav chemických procesů Kontakt Eva Jirsová, jirsova@icpf.cas.cz, Tel.: 220 390 227 Rok sběru 2021 Elektronická adresa http://hdl.handle.net/11104/0309759
Počet záznamů: 1