Periodic Reporting for period 1 - PHOTO-ITU (Merging enantioselective isothiourea catalysis with visible-light photoactivation for the synthesis of biologically-relevant chiral molecules)
Periodo di rendicontazione: 2021-03-01 al 2023-02-28
Currently, many of the important chemicals found in medicine and agriculture are manufactured using long-known techniques that rely on the use of expensive, toxic metals, and the use of thermal energy in the form of heat. A key aim for chemists is to both expand the toolbox of chemistry to enable the synthesis of new chemicals, and to improve the efficiency and sustainability of manufacturing. In very recent times, the use of visible light as a source of energy to drive chemical reactions has become a topic of great interest, since both new reactions can be developed and without the requirement for excessive heating. Visible light is a far more sustainable source of energy compared to heat.
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.
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.
The work that was carried out during the project includes:
• 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.
• 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.
The socio-economic impacts of the project are mainly related to the potential for the technology to be exploited in an industrial setting. Since the output of the project has been published, companies are free to use this technology in their operations, which may increase their economic efficiency and/or the sustainability of their practices for the production of fine chemicals.
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.
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.