Preserving precise choreography of bonds in Z-stereoretentive olefin metathesis by using quinoxaline-2,3-dithiolate ligand

Łukasz Grzesiński, Maryana Nadirova, Jannick Guschlbauer, Artur Brotons-Rufes, Albert Poater (), Anna Kajetanowicz () and Karol Grela ()
Additional contact information
Łukasz Grzesiński: University of Warsaw
Maryana Nadirova: University of Warsaw
Jannick Guschlbauer: University of Warsaw
Artur Brotons-Rufes: Universitat de Girona
Albert Poater: Universitat de Girona
Anna Kajetanowicz: University of Warsaw
Karol Grela: University of Warsaw

Nature Communications, 2024, vol. 15, issue 1, 1-12

Abstract: Abstract The Z-alkene geometry is prevalent in various chemical compounds, including numerous building blocks, fine chemicals, and natural products. Unfortunately, established Mo, W, and Ru Z-selective catalysts lose their selectivity at high temperatures required for industrial processes like reactive distillation, which limits their synthetic applications. To address this issue, we develop a catalyst capable of providing Z-alkenes with high selectivity under harsh conditions. Our research reveals a dithiolate ligand that, stabilised by resonance, delivers high selectivity at temperatures up to 150 °C in concentrated mixtures. This distinguishes the dithioquinoxaline complex from existing Z-selective catalysts. Notably, this trait does not compromise the new catalyst’s usability under classical conditions, matching the activity of known stereoretentive catalysts. Density Functional Theory calculations were employed to understand the reaction mechanism and selectivity, and to investigate the poisoning that the catalyst may undergo and how it competes with catalytic activity. Furthermore, the quinoxaline-based catalyst enables the valorisation of bio-sourced alkene feedstocks and the production of agricultural sex pheromones for pest control.

Date: 2024
References: View references in EconPapers View complete reference list from CitEc
Citations:

Downloads: (external link)
https://www.nature.com/articles/s41467-024-52876-4 Abstract (text/html)

Related works:
This item may be available elsewhere in EconPapers: Search for items with the same title.

Export reference: BibTeX RIS (EndNote, ProCite, RefMan) HTML/Text

Persistent link: https://EconPapers.repec.org/RePEc:nat:natcom:v:15:y:2024:i:1:d:10.1038_s41467-024-52876-4

Ordering information: This journal article can be ordered from
https://www.nature.com/ncomms/

DOI: 10.1038/s41467-024-52876-4

Access Statistics for this article

Nature Communications is currently edited by Nathalie Le Bot, Enda Bergin and Fiona Gillespie

More articles in Nature Communications from Nature
Bibliographic data for series maintained by Sonal Shukla () and Springer Nature Abstracting and Indexing ().