TY - JOUR AU - Maestro, Aitor AU - Malviya, Bhanwar K. AU - Auer, Gerald AU - Ötvös, Sándor Balázs AU - Kappe, C. Oliver TI - A robust heterogeneous chiral phosphoric acid enables multi decagram scale production of optically active N , S -ketals JF - GREEN CHEMISTRY J2 - GREEN CHEM PY - 2024 SN - 1463-9262 DO - 10.1039/D4GC00019F UR - https://m2.mtmt.hu/api/publication/34799035 ID - 34799035 AB - A multi-decagram scale synthesis of enantioenriched N,S -ketals was achieved by using a robust heterogeneous organocatalyst. A new reactor design was crucial to enable the scaling up of this reaction while the overall catalyst loading below 0.1%. LA - English DB - MTMT ER - TY - JOUR AU - Kocsis, Marianna AU - Baán, Kornélia AU - Ötvös, Sándor Balázs AU - Kukovecz, Ákos AU - Kónya, Zoltán AU - Sipos, Pál Miklós AU - Pálinkó, István AU - Varga, Gábor TI - Sustainable synthesis of azobenzenes, quinolines and quinoxalines via oxidative dehydrogenative couplings catalysed by reusable transition metal oxide–Bi( iii ) cooperative catalysts JF - CATALYSIS SCIENCE & TECHNOLOGY J2 - CATAL SCIENCE & TECHNOLOGY VL - 13 PY - 2023 IS - 10 SP - 3069 EP - 3083 PG - 15 SN - 2044-4753 DO - 10.1039/D3CY00327B UR - https://m2.mtmt.hu/api/publication/33763892 ID - 33763892 AB - Heterogeneous catalytic oxidative dehydrogenative processes for N-heterocycles are presented, which enable waste-minimized (additive-, oxidant-, base-free), efficient cyclisations/couplings via transition metal oxide–Bi( iii ) cooperative catalysis. LA - English DB - MTMT ER - TY - JOUR AU - Kocsis, Marianna AU - Szabados, Márton AU - Ötvös, Sándor Balázs AU - Samu, Gergely Ferenc AU - Fogarassy, Zsolt AU - Pécz, Béla AU - Kukovecz, Ákos AU - Kónya, Zoltán AU - Sipos, Pál Miklós AU - Pálinkó, István AU - Varga, Gábor TI - Selective production of imines and benzimidazoles by cooperative bismuth(III)/transition metal ion catalysis JF - JOURNAL OF CATALYSIS J2 - J CATAL VL - 414 PY - 2022 SP - 163 EP - 178 PG - 16 SN - 0021-9517 DO - 10.1016/j.jcat.2022.09.008 UR - https://m2.mtmt.hu/api/publication/33097696 ID - 33097696 AB - Cooperative Bi(III)/Co(II) and Bi(III)/Mn(II) heterogeneous catalysts have been developed enabling efficient oxidative annulations for preparing both cross-coupled imines and benzimidazoles under ambient conditions in an atom-economic and time-efficient manner, involving ambient air as oxidant and without the need of any other additives. This is the first synergistic Lewis acid/transition metal catalyzed annulation which is potentiated by the interfaces between the building blocks of the catalysts. To achieve our goals, a useful fabrication process has been developed to heterogenize the transition metal ions via strong interactions on well-known Sillèn-type bismuth subcarbonate (bismutite). Their reusability, activity and selectivity as well as water-tolerance have made them potential competitors to effective heterogeneous/homogeneous catalysts reported previously. LA - English DB - MTMT ER - TY - JOUR AU - Nagy, Bence S. AU - Llanes, Patricia AU - Pericas, Miquel A. AU - Kappe, C. Oliver AU - Ötvös, Sándor Balázs TI - Enantioselective Flow Synthesis of Rolipram Enabled by a Telescoped Asymmetric Conjugate Addition-Oxidative Aldehyde Esterification Sequence Using in Situ-Generated Persulfuric Acid as Oxidant JF - ORGANIC LETTERS J2 - ORG LETT VL - 24 PY - 2022 IS - 4 SP - 1066 EP - 1071 PG - 6 SN - 1523-7060 DO - 10.1021/acs.orglett.1c04300 UR - https://m2.mtmt.hu/api/publication/32883635 ID - 32883635 AB - A novel approach is reported for the enantioselective flow synthesis of rolipram comprising a telescoped asymmetric conjugate addition-oxidative aldehyde esterification sequence followed by trichlorosilane-mediated nitro group reduction and concomitant lactamization. The telescoped process takes advantage of a polystyrene-supported chiral organocatalyst along with in situ-generated persulfuric acid as a robust and scalable oxidant for direct aldehyde esterification. This approach demonstrates significantly improved productivity compared with earlier methodologies while ensuring environmentally benign metal-free conditions. LA - English DB - MTMT ER - TY - JOUR AU - Ötvös, Sándor Balázs AU - Kappe, C. Oliver TI - Continuous flow asymmetric synthesis of chiral active pharmaceutical ingredients and their advanced intermediates JF - GREEN CHEMISTRY J2 - GREEN CHEM VL - 23 PY - 2021 IS - 17 SP - 6117 EP - 6138 PG - 22 SN - 1463-9262 DO - 10.1039/d1gc01615f UR - https://m2.mtmt.hu/api/publication/32368621 ID - 32368621 AB - Catalytic enantioselective transformations provide well-established and direct access to stereogenic synthons that are broadly distributed among active pharmaceutical ingredients (APIs). These reactions have been demonstrated to benefit considerably from the merits of continuous processing and microreactor technology. Over the past few years, continuous flow enantioselective catalysis has grown into a mature field and has found diverse applications in asymmetric synthesis of pharmaceutically active substances. The present review therefore surveys flow chemistry-based approaches for the synthesis of chiral APIs and their advanced stereogenic intermediates, covering the utilization of biocatalysis, organometallic catalysis and metal-free organocatalysis to introduce asymmetry in continuously operated systems. Single-step processes, interrupted multistep flow syntheses, combined batch/flow processes and uninterrupted one-flow syntheses are discussed herein. LA - English DB - MTMT ER - TY - JOUR AU - Szécsényi, Zsanett AU - Fülöp, Ferenc AU - Ötvös, Sándor Balázs TI - Bismuth Subnitrate-Catalyzed Markovnikov-Type Alkyne Hydrations under Batch and Continuous Flow Conditions JF - MOLECULES J2 - MOLECULES VL - 26 PY - 2021 IS - 10 PG - 12 SN - 1420-3049 DO - 10.3390/molecules26102864 UR - https://m2.mtmt.hu/api/publication/32242848 ID - 32242848 AB - Bismuth subnitrate is reported herein as a simple and efficient catalyst for the atom-economical synthesis of methyl ketones via Markovnikov-type alkyne hydration. Besides an effective batch process under reasonably mild conditions, a chemically intensified continuous flow protocol was also developed in a packed-bed system. The applicability of the methodologies was demonstrated through hydration of a diverse set of terminal acetylenes. By simply switching the reaction medium from methanol to methanol-d(4), valuable trideuteromethyl ketones were also prepared. Due to the ready availability and nontoxicity of the heterogeneous catalyst, which eliminated the need for any special additives and/or harmful reagents, the presented processes display significant advances in terms of practicality and sustainability. LA - English DB - MTMT ER - TY - JOUR AU - Kocsis, Marianna AU - Ötvös, Sándor Balázs AU - Samu, Gergely Ferenc AU - Fogarassy, Zsolt AU - Pécz, Béla AU - Kukovecz, Ákos AU - Kónya, Zoltán AU - Sipos, Pál Miklós AU - Pálinkó, István AU - Varga, Gábor TI - Copper-Loaded Layered Bismuth Subcarbonate—Efficient Multifunctional Heterogeneous Catalyst for Concerted C–S/C–N Heterocyclization JF - ACS APPLIED MATERIALS & INTERFACES J2 - ACS APPL MATER INTER VL - 13 PY - 2021 IS - 36 SP - 42650 EP - 42661 PG - 12 SN - 1944-8244 DO - 10.1021/acsami.1c09234 UR - https://m2.mtmt.hu/api/publication/32180565 ID - 32180565 LA - English DB - MTMT ER - TY - JOUR AU - Girst, Gábor AU - Ötvös, Sándor Balázs AU - Fülöp, Ferenc AU - Balogh, György Tibor AU - Hunyadi, Attila TI - Pharmacokinetics-Driven Evaluation of the Antioxidant Activity of Curcuminoids and Their Major Reduced Metabolites—A Medicinal Chemistry Approach JF - MOLECULES J2 - MOLECULES VL - 26 PY - 2021 IS - 12 PG - 11 SN - 1420-3049 DO - 10.3390/molecules26123542 UR - https://m2.mtmt.hu/api/publication/32086896 ID - 32086896 N1 - Institute of Pharmacognosy, Interdisciplinary Centre of Excellence, University of Szeged, Szeged, H-6720, Hungary Institute of Pharmaceutical Chemistry, University of Szeged, Szeged, H-6720, Hungary Institute of Chemistry, University of Graz, NAWI Graz, Heinrichstrasse 28, Graz, A-8010, Austria Department of Chemical and Environmental Process Engineering, Budapest University of Technology and Economics, Budapest, H-1111, Hungary Department of Pharmacodynamics and Biopharmacy, University of Szeged, Szeged, H-6720, Hungary Interdisciplinary Centre of Natural Products, University of Szeged, Szeged, H-6720, Hungary Export Date: 3 November 2021 CODEN: MOLEF Correspondence Address: Balogh, G.T.; Department of Chemical and Environmental Process Engineering, Hungary; email: balogh.gyorgy@vbk.bme.hu Correspondence Address: Hunyadi, A.; Institute of Pharmacognosy, Hungary; email: hunyadi.a@pharmacognosy.hu LA - English DB - MTMT ER - TY - JOUR AU - Mészáros, Rebeka Ildikó AU - Márton, András AU - Szabados, Márton AU - Varga, Gábor AU - Kónya, Zoltán AU - Kukovecz, Ákos AU - Fülöp, Ferenc AU - Pálinkó, István AU - Ötvös, Sándor Balázs TI - Exploiting a Silver–Bismuth Hybrid Material as Heterogeneous Noble Metal Catalyst for Decarboxylations and Decarboxylative Deuterations of Carboxylic Acids under Batch and Continuous Flow Conditions JF - GREEN CHEMISTRY J2 - GREEN CHEM VL - 23 PY - 2021 IS - 13 SP - 4685 EP - 4696 PG - 12 SN - 1463-9262 DO - 10.1039/D1GC00924A UR - https://m2.mtmt.hu/api/publication/32028714 ID - 32028714 LA - English DB - MTMT ER - TY - JOUR AU - Mészáros, Rebeka Ildikó AU - Ötvös, Sándor Balázs AU - Varga, Gábor AU - Böszörményi, Éva AU - Kocsis, Marianna AU - Karádi, Krisztina Anna AU - Kónya, Zoltán AU - Kukovecz, Ákos AU - Pálinkó, István AU - Fülöp, Ferenc TI - A mineralogically-inspired silver–bismuth hybrid material: Structure, stability and application for catalytic benzyl alcohol dehydrogenations under continuous flow conditions JF - MOLECULAR CATALYSIS J2 - MOL CATAL VL - 498 PY - 2020 PG - 8 SN - 2468-8231 DO - 10.1016/j.mcat.2020.111263 UR - https://m2.mtmt.hu/api/publication/31603447 ID - 31603447 LA - English DB - MTMT ER -