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Synthesis, catalytic activity and medium fluorous recycle of fluorous analogues of PEPPSI catalysts
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SYSNO ASEP 0525654 Document Type J - Journal Article R&D Document Type Journal Article Subsidiary J Článek ve WOS Title Synthesis, catalytic activity and medium fluorous recycle of fluorous analogues of PEPPSI catalysts Author(s) Šimůnek, O. (CZ)
Rybáčková, M. (CZ)
Svoboda, Martin (UOCHB-X) ORCID
Kvíčala, J. (CZ)Article number 109588 Source Title Journal of Fluorine Chemistry. - : Elsevier - ISSN 0022-1139
Roč. 236, Aug (2020)Number of pages 14 s. Language eng - English Country CH - Switzerland Keywords palladium complex ; PEPPSI ; Suzuki-Miyaura coupling ; perfluorooxaalkanoate ; fluorous ; recycle Subject RIV CC - Organic Chemistry OECD category Organic chemistry Method of publishing Limited access Institutional support UOCHB-X - RVO:61388963 UT WOS 000551145100016 EID SCOPUS 85086442977 DOI 10.1016/j.jfluchem.2020.109588 Annotation PEPPSI complexes are air and moisture stable Pd catalysts, which can be used conveniently in many coupling reactions. With the aim to obtain Pd catalysts recyclable by fluorous separation methods, we modified the structure of commercial PEPPSI complexes by per- or polyfluoroalkylation in various positions. The modifications included the use of a linear polyfluoroalkyl group instead of one aryl group on the NHC ligand, perfluoroalkylation of pyridine ligand, and substitution of chloride ligands on Pd for perfluoroalkanoates or perfluoropolyoxaalkanoates. Comparison of catalytic activity of commercial catalysts with the modified ones in Suzuki-Miyaura cross-coupling reactions showed that the fluorous modifications mostly resulted in the increase of catalytic activity. Moreover, polyfluoroalkylation enabled efficient medium fluorous recycle of the modified catalysts using a two phase aqueous DMF/HFE 7500 ether system. Workplace Institute of Organic Chemistry and Biochemistry Contact asep@uochb.cas.cz ; Kateřina Šperková, Tel.: 232 002 584 ; Jana Procházková, Tel.: 220 183 418 Year of Publishing 2021 Electronic address https://www.sciencedirect.com/science/article/pii/S0022113920302864?via%3Dihub
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