Periodic Reporting for period 1 - PHOTO-ITU (Merging enantioselective isothiourea catalysis with visible-light photoactivation for the synthesis of biologically-relevant chiral molecules)
Période du rapport: 2021-03-01 au 2023-02-28
In this regard, the aim of the project was to investigate the use of visible light for the discovery of new chemical reactions. Specifically, the aim was to use isothiourea catalysts (organocatalysts), which are cheap, non-toxic, and easily made, and combine their use with photochemical activation, to synthesize molecules which may be of biological importance.
This was realized by combining isothiourea catalysts with photoredox catalysis, which has enabled the construction of complex chiral molecules from readily available and cheap starting materials. New isothiourea catalysts were developed and used in this technology alongside organic, metal-free photoredox catalysts, which constitutes a sustainable method which has been shown to be useful for making biologically relevant molecules.
New ways to make biologically active chemicals are sought-after in both academic and industrial settings. This is due to the potential advantages of newly discovered methods that may include reduced cost, toxicity, environmental impact, safety risks and operational difficulties. From an industrial point of view, the project has led to the development of a sustainable method for the production of chiral chemical products that may be of interest to the pharmaceutical and agrochemical industries. Therefore, the project has the potential to impact society beneficially by improving the manufacture of chemicals.
The overall objectives for the project were to establish a platform for the use of visible light as an energy source in isothiourea-catalysed chemical reactions.
• Reaction discovery of the enantioselective radical conjugate addition
• Optimization of the reaction (all reaction variables and parameters)
• Exploitation of the reaction in the synthesis of 34 complex enantioenriched products
• Derivatization of some products to demonstrate applicability
• Mechanistic investigation of the reaction, including analysis via photophysical, electrochemical, spectroscopic and physical organic chemical analysis.
In addition, the academic value of the work is likely to be significant. The work has been published in a high-impact chemistry journal and disseminated at a high-profile international conference. Global reach has been enhanced through sharing on social media platforms. The work represents a conceptual advance in the fields of asymmetric organocatalysis and photochemistry, advancing the state-of-the-art in enantioselective photochemical reactions.