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N-heterocyclic carbenes with three and six fluorous ponytails and their highly fluorophilic Rh and Ir complexes
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SYSNO ASEP 0569339 Document Type J - Journal Article R&D Document Type Journal Article Subsidiary J Článek ve WOS Title N-heterocyclic carbenes with three and six fluorous ponytails and their highly fluorophilic Rh and Ir complexes Author(s) Dušková, T. (CZ)
Prajapati, D.S. (CZ)
Kaule, P. (CZ)
Červenková Šťastná, Lucie (UCHP-M) RID, ORCID, SAI
Strašák, Tomáš (UCHP-M) RID, ORCID, SAI
Čermák, Jan (UCHP-M) RID, ORCID, SAIArticle number 122605 Source Title Journal of Organometallic Chemistry. - : Elsevier - ISSN 0022-328X
Roč. 986, FEB 15 (2023)Number of pages 9 s. Language eng - English Country CH - Switzerland Keywords N-heterocyclic carbene ; fluorous chemistry ; rhodium complexes ; iridium complexes OECD category Organic chemistry Method of publishing Open access with time embargo (16.02.2025) Institutional support UCHP-M - RVO:67985858 UT WOS 000915633600001 EID SCOPUS 85145830029 DOI 10.1016/j.jorganchem.2022.122605 Annotation Reactions of 1-methylimidazole and 1-(1-methylethyl)imidazole with (3-iodopropyl)tris(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl)silane gave the corresponding 1-alkyl-3-(3-(tris(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl) silyl) propyl) imidazolium iodides 1 and 2. Reaction of imidazole in excess with (3-iodopropyl)tris(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl)silane afforded 1-(3-(tris(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl) silyl) propyl) imidazole 3 which was further reacted with (3-iodopropyl)tris(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl)silane to produce the doubly tagged 1,3-bis[3-(tris(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl) silyl) propyl] imidazolium iodide 4 and by anion exchange a tetrafluoroborate salt 5. The prepared imidazolium iodides 1,2, and 4 were then used as pre-cursors in synthesis of chlorido(cycloocta-1,5-diene)rhodium or-iridium complexes bearing Nheterocyclic carbenes with one 3-[tris(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl)silyl]propyl-substituent and methyl-, 1-methylethyl-and another 3-[ tris(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl )silyl]propyl-substituent on nitrogens, 6 11. The metal complexes were equimolar mixtures of conformational enantiomers as was best documented by the 1H NMR signals of diastereotopic CH2 protons next to nitrogen. Fluorophilicity fi as the natural logarithm of partition coefficient Pi between fluorous and organic phase of the complexes was determined in the standard solvent system (perfluoro)methylcyclohexane/toluene. All the complexes are fluorophilic with variation of fi between 0.96 and 4.06, the complexes with high values may be classified as highly fluorophilic (heavy fluorous).(c) 2022 Elsevier B.V. All rights reserved. Workplace Institute of Chemical Process Fundamentals Contact Eva Jirsová, jirsova@icpf.cas.cz, Tel.: 220 390 227 Year of Publishing 2024 Electronic address https://hdl.handle.net/11104/0340756
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