OPEN Repository
Welcome to OPEN - the Repository of Open Scientific Publications, run by the Interdisciplinary Centre for Mathematical and Computational Modelling, University of Warsaw, previously operating as the CeON Repository. The Repository enables Polish researchers from all fields to openly share their articles, books, conference materials, reports, doctoral theses, and other scientific texts.
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22936 archived items
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Recent Submissions
Item
Aqueous Micellar Environment Impacts the Co-Catalyzed Phototransformation: A Case Study
(American Chemical Society, 2024) Wincenciuk, Aleksandra; Cmoch, Piotr; Giedyk, Maciej; Andersson, Martin P.; Gryko, Dorota; Institute of Organic Chemistry, Polish Academy of Sciences; Center for Integrative Petroleum Research, King Fahd University of Petroleum and Minerals, Kingdom of Saudi Arabia
In recent years, methodologies that rely on water as the reaction medium have gained considerable attention. The unique properties of micellar solutions were shown to improve the regio-, stereo-, and chemoselectivity of different transformations. Herein, we demonstrate that the aqueous environment is a suitable medium for a visible light driven cobalt-catalyzed reaction involving radical species. In this system, reduced vitamin B12 reacts with alkyl halides, generating radicals that are trapped by the lipophilic olefin present in the Stern layer. A series of NMR measurements and theoretical studies revealed the location of reaction components in the micellar system.
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Aryl versus Alkyl Redox-Active Diazoacetates ─ Light-Induced C–H Insertion or 1,2-Rearrangement
(American Chemical Society, 2023) Santiago, João V.; Orłowska, Katarzyna; Ociepa, Michał; Gryko, Dorota; Institute of Organic Chemistry, Polish Academy of Sciences
Diazo compounds with redox-active leaving groups are versatile reagents for orthogonal functionalizations, previously utilized in the Rh-catalyzed synthesis of highly substituted cyclopropanes. Photochemical activation of aryl-substituted diazoacetates generates carbenes, whereas redox-active esters can furnish C-radicals via the photoexcitation of EDA complexes. However, the photochemical behavior of these two functionalities, while present in one molecule, remains to be defined. We demonstrate that under light irradiation, reactions occur only on the diazomoiety, leaving the NHPI functionality intact. Not only aryl- but also alkyl-substituted NHPI diazoacetates are activated by blue light; either C−H insertion or the hydrogen/carbon 1,2-rearrangement occurs depending on the aryl/alkyl group.
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Porphyrins as Promising Photocatalysts for Red-Light-Induced Functionalizations of Biomolecules
(American Chemical Society, 2022) Rybicka-Jasińska, Katarzyna; Wdowik, Tomasz; Łuczak, Klaudia; Wierzba, Aleksandra J.; Drapała, Olga; Gryko, Dorota; Institute of Organic Chemistry, Polish Academy of Sciences
Red-light enables deeper material penetration, which is important for biological applications and has consequences for chemical synthesis. Therefore, the search for new photocatalysts that absorb in this region is crucial. Despite the undeniable utility of porphyrins in blue- and green-light-induced energy- and electron-transfer processes, they are also perfectly suited for redlight applications. Herein, we describe free-base porphyrins as photoredox catalysts for red-light-induced organic transformations. They can act as both photooxidants and photoreductants and can accomplish the synthesis of biaryls once merged with Pd-catalysis. The developed methodology holds promise for broader applications, as the heme-based protoporphyrin is used as a photocatalyst and reactions can be realized in aqueous conditions.
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Site-Selective, Photocatalytic Vinylogous Amidation of Enones
(American Chemical Society, 2022) Szabó, Kitti Franciska; Goliszewska, Katarzyna; Szurmak, Jakub; Rybicka-Jasińska, Katarzyna; Gryko, Dorota; Institute of Organic Chemistry, Polish Academy of Sciences
Despite the broad interest in organic compounds possessing a γ-aminocarbonyl motif, limited strategies for their synthesis have been reported. Herein, we describe a mild and efficient method for the site-selective amidation of unsaturated enones with electrophilic N-centered radicals as a key intermediate. The photocatalytic vinylogous reaction of dienolates with N-amino pyridinium salts affords γ-amido carbonyl compounds. This process is high-yielding, scalable, and tolerates a broad range of unsaturated α,β-unsaturated carbonyls, including biologically relevant compounds, as starting materials.
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C−C Bond Forming Reactions Enabled by Vitamin B12 - Opportunities and Challenges
(American Chemical Society, 2022) Wdowik, Tomasz; Gryko, Dorota; Institute of Organic Chemistry, Polish Academy of Sciences
Cobalt not only is an essential micronutrient for mammals but also marks itself as important in organic synthesis, especially in the field of catalysis. Various useful reactions, such as alkene hydroformylation, hydrogenation, heterofunctionalizations of carbon–carbon double bonds, C–H activation, and cross-coupling reactions, have been realized with the aid of this metal. At the same time, cobalt deserves special attention as a catalyst for radical processes; in fact, in the form of vitamin B12, it was designed by Nature as a reversible carrier for radicals. Since this molecule is a native Co-complex, it is very attractive for the development of sustainable transformations, and it has already been demonstrated that vitamin B12 and its derivatives mediate numerous reactions that have found applications in both the construction of complex molecules and the degradation of polyhalogenated pollutants. However, in this Perspective, we focus the readers’ attention on radical C–C bond forming reactions catalyzed by vitamin B12, which are particularly important as a tool for the synthesis of important molecules in a greener manner. We also ponder over the challenges that remain to be addressed and the solutions that are expected to come.
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