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Zirconium-Catalyzed Remote Cleavage of Alkenyl Cyclopropanes
Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry for Life Sciences. (Jan Streuff)ORCID iD: 0000-0002-1210-4654
Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry for Life Sciences. Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Preparative Medicinal Chemistry. (Jan Streuff)
Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry for Life Sciences. (Jan Streuff)
Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry for Life Sciences, Organic Chemistry. (Jan Streuff)ORCID iD: 0000-0002-8320-4353
(English)Manuscript (preprint) (Other academic)
Keywords [en]
catalysis, C-C cleavage, cyclopropane, silylation, zirconium
National Category
Organic Chemistry
Research subject
Chemistry with specialization in Organic Chemistry
Identifiers
URN: urn:nbn:se:uu:diva-595704OAI: oai:DiVA.org:uu-595704DiVA, id: diva2:2093319
Available from: 2026-08-18 Created: 2026-08-18 Last updated: 2026-08-18
In thesis
1. Development of zirconium hydride catalyzed migratory C-C cleavage and hydrosilylation reactions
Open this publication in new window or tab >>Development of zirconium hydride catalyzed migratory C-C cleavage and hydrosilylation reactions
2026 (English)Doctoral thesis, comprehensive summary (Other academic)
Abstract [en]

Catalysis based on earth-abundant early transition metals has emerged as a sustainable alternative to traditional late transition-metal catalysis. In this context, zirconium(IV) complexes stand out for their unique reactivity, enabling both functionalization and cleavage reactions. 

This thesis describes the development of two zirconocene-catalyzed methodologies together with the identification of a practical strategy for the in situ generation of the active zirconium hydride catalyst.

The first project focuses on the development of a new zirconium-catalyzed C-C bond cleavage reaction of unactivated alkenylcyclopropanes. Depending on the hydride source and conditions, the reaction yields either the corresponding open-chain product or its hydrosilylated derivative. By exploiting the “chain-walking” ability of zirconocene hydride complexes, cyclopropanes distant up to eight carbons from the alkene unit could be successfully converted into the corresponding products. 

The second project involves the development of a new zirconium catalyzed hydrosilylation reaction of terminal and internal alkenes. This method employs the commercially available precatalyst Cp2ZrCl2 together with LiOMe and silanes as mild catalyst activators, providing a practical alternative to existing late transition-metal based methods. Mechanistic investigations support a pathway involving a zirconium(IV) species. 

Interestingly, in both projects LiOMe and silane emerged as unifying activation strategy for accessing the catalytically active zirconocene hydride species, enabling both bond-forming and bond-cleavage transformations under operationally simple conditions.

Place, publisher, year, edition, pages
Uppsala: Acta Universitatis Upsaliensis, 2026. p. 107
Series
Digital Comprehensive Summaries of Uppsala Dissertations from the Faculty of Science and Technology, ISSN 1651-6214 ; 2708
Keywords
catalysis, C-C cleavage, cyclopropane, hydrosilylation, zirconium, zirconium walk
National Category
Organic Chemistry
Research subject
Chemistry with specialization in Organic Chemistry
Identifiers
urn:nbn:se:uu:diva-595721 (URN)978-91-513-2931-4 (ISBN)
Public defence
2026-10-06, A1:107a, BMC, Husargatan 3, Uppsala, 09:00 (English)
Opponent
Supervisors
Available from: 2026-09-14 Created: 2026-08-18 Last updated: 2026-09-14

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Luongo, Orsola A.Matt, ChristofStreuff, Jan

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CiteExportLink to record
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Cite
Citation style
  • apa
  • ieee
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  • vancouver
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More styles
Language
  • de-DE
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  • en-US
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  • nn-NB
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Output format
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