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Electrochemical Generation of Hydrides over a Nickel Foam for Z-Stereoselective Semihydrogenation/deuteration of Functionalized Alkynes
Stockholm University, Faculty of Science, Department of Organic Chemistry.ORCID iD: 0000-0003-2700-2391
Stockholm University, Faculty of Science, Department of Organic Chemistry.
Stockholm University, Faculty of Science, Department of Organic Chemistry.
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(English)Manuscript (preprint) (Other academic)
Abstract [en]

Selective reduction strategies based on abundant-metal catalysts are very important in the production of chemicals. In this paper, we present a method for the electrochemical semihydrogenation and semideuteration of alkynes to form Z-alkenes using a simplenickel foam as catalyst and H3O+or D3O+as sources of hydrogen or deuterium. Good yields and excellent stereoselectivities (Z/E up to 20:1) are obtained under very mild reaction conditions. The reaction works with terminal and nonterminal alkynes, and with alkynes containing easily reducible functional groups, such as carbonyl groups, and aryl chlorides, bromides, and even iodides. The nickel-foam electrocatalyst can be recycled up to 14 times without any change in its catalytic properties.

Keywords [en]
nickel-foam electrocatalysis, alkyne, hydrogenation, deuteration
National Category
Organic Chemistry
Research subject
Organic Chemistry
Identifiers
URN: urn:nbn:se:su:diva-198073OAI: oai:DiVA.org:su-198073DiVA, id: diva2:1605941
Available from: 2021-10-26 Created: 2021-10-26 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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Available from: 2021-11-17 Created: 2021-10-26 Last updated: 2022-02-25Bibliographically approved

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Valiente, AlejandroMartinez-Pardo, PabloKaur, GurpreetMartín-Matute, Belen

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