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

• DOI: 10.1038/s41467-024-52876-4
• Publication Date: 2024-10-17T19:03:09Z
• Authors: Łukasz Grzesiński; Maryana Nadirova; Jannick Guschlbauer; Artur Brotons-Rufes; Albert Poater; Anna Kajetanowicz; Karol Grela
• Keywords: Olefin Metathesis; Quinoxaline; Choreography

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