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Aerobic Homocoupling of Arylboronic Acids Catalyzed by Regenerable Pd(II)@MIL-88B-NH2(Cr)
Stockholm University, Faculty of Science, Department of Organic Chemistry.ORCID iD: 0000-0003-2700-2391
Stockholm University, Faculty of Science, Department of Organic Chemistry.ORCID iD: 0000-0003-0024-1392
Stockholm University, Faculty of Science, Department of Organic Chemistry.ORCID iD: 0000-0002-1729-598X
Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK).ORCID iD: 0000-0001-7286-1211
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2019 (English)In: ChemCatChem, ISSN 1867-3880, E-ISSN 1867-3899, Vol. 11, no 16, p. 3933-3940Article in journal (Refereed) Published
Abstract [en]

A fast and operationally simple method for the aerobic homocoupling of arylboronic acids is described. The process is catalyzed by Pd(II) complexes supported on the metal-organic framework MIL-88B-NH2(Cr). The benefits of this approach include the use of a benign oxidant/solvent mixture at room temperature with catalytic amounts of base, easy recovery of the catalyst, and easy isolation of the products. Very high conversions and good yields were achieved for a variety of substrates, and the process was also carried out on a larger scale with the same efficiency. The catalyst was found to suffer deactivation due to progressive reduction and agglomeration of palladium into inactive metal clusters/particles. An innovative procedure for the oxidative redispersion and regeneration of the active Pd(II)@MOF species is presented. 

Place, publisher, year, edition, pages
2019. Vol. 11, no 16, p. 3933-3940
Keywords [en]
aerobic homocoupling, catalyst deactivation, metal-organic frameworks, oxidative redispersion, catalyst regeneration
National Category
Chemical Sciences
Identifiers
URN: urn:nbn:se:su:diva-191586DOI: 10.1002/cctc.201900556ISI: 000498036500041OAI: oai:DiVA.org:su-191586DiVA, id: diva2:1540124
Funder
Swedish Research CouncilGöran Gustafsson Foundation for Research in Natural Sciences and MedicineKnut and Alice Wallenberg FoundationAvailable from: 2021-03-26 Created: 2021-03-26 Last updated: 2022-02-25Bibliographically approved
In thesis
1. Catalytic and Electrocatalytic Transformations with Palladium and Nickel: Scope and mechanistic investigations
Open this publication in new window or tab >>Catalytic and Electrocatalytic Transformations with Palladium and Nickel: Scope and mechanistic investigations
2021 (English)Doctoral thesis, comprehensive summary (Other academic)
Abstract [en]

The work presented in this thesis is based on methodology development and mechanistic investigations using heterogeneous palladium and nickel catalysts. Following the introduction (Chapter 1), Chapter 2 presents a summary of the synthesis and characterization of the MOF-supported Pd catalysts (Pd @ MOF) that are used in this thesis. Chapters 3, 4 and 5 are based on the use of heterogeneous Pd @ MOF catalysts for CC bond forming reactions, whilst Chapter 6 deals with the use of nickel foam for hydrogenation reactions. 

In Chapter 3, the speciation of the ligandless Suzuki-Miyaura reaction catalyzed by Pd @ MOF is investigated. Here, questions regarding the composition, structure and reactivity of leached palladium are studied by means of electrospray ionization mass spectrometry (ESI-MS), density-functional theory (DFT) calculations, nuclear magnetic resonance (NMR) spectroscopy and scanning-transmission electron microscopy (STEM). (Paper I)

The next chapter (Chapter 4) deals with the study of the Mizoroki-Heck reaction catalyzed by Pd @ MOF under working conditions. In this study, catalyst activation, catalyst deactivation and the role of the MOF support are studied. (Paper II) 

Chapter 5 concerns the use of MOF-supported Pd (II) complexes for the aerobic homocoupling of boronic acids. A mild oxidation method for regenerating active catalytic palladium species, which enables its recyclability, is described. (Paper III)

The last chapter (Chapter 6) describes the use of a commercially available nickel foam for the stereoselective semireduction of alkynes using electrochemically generated hydrides from acidic water. As the method tolerates numerous functional groups, it could be applied to a large variety of alkynes. The use of deuterated solvents provided easy access to a library of deuterated Z -olefins. (Paper IV)

Place, publisher, year, edition, pages
Stockholm: Department of Organic Chemistry, Stockholm University, 2021. p. 78
Keywords
Organic Chemistry, Heterogeneous Catalysis, Metal-organic frameworks, Nickel, Palladium, Electrocatalysis, Cross-coupling, Hydrogenation
National Category
Organic Chemistry
Research subject
Organic Chemistry
Identifiers
urn:nbn:se:su:diva-198076 (URN)978-91-7911-668-2 (ISBN)978-91-7911-669-9 (ISBN)
Public defence
2021-12-10, Magnélisalen, Kemiska övningslaboratoriet, Svante Arrhenius väg 16 B and online via Zoom, public link is available at the department website, Stockholm, 10:00 (English)
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Supervisors
Available from: 2021-11-17 Created: 2021-10-26 Last updated: 2022-02-25Bibliographically approved

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Valiente, AlejandroCarrasco, SergioSanz-Marco, AmparoTai, Cheuk-WaiBermejo Gómez, AntonioMartín-Matute, Belén

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Valiente, AlejandroCarrasco, SergioSanz-Marco, AmparoTai, Cheuk-WaiBermejo Gómez, AntonioMartín-Matute, Belén
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