| EPSRC Reference: |
EP/X013081/1 |
| Title: |
Catalytic Hydrofluorination for the Assembly of Chiral Fluorinated Building Blocks |
| Principal Investigator: |
Johnston, Dr C |
| Other Investigators: |
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| Researcher Co-Investigators: |
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| Project Partners: |
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| Department: |
Chemistry |
| Organisation: |
University of St Andrews |
| Scheme: |
New Investigator Award |
| Starts: |
01 July 2023 |
Ends: |
30 June 2026 |
Value (£): |
415,207
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| EPSRC Research Topic Classifications: |
| Catalysis & Applied Catalysis |
Chemical Synthetic Methodology |
| Co-ordination Chemistry |
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| EPSRC Industrial Sector Classifications: |
| No relevance to Underpinning Sectors |
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| Panel History: |
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Summary on Grant Application Form |
The linking of molecules to produce desirable products, such as pharmaceuticals and agrochemicals, has undoubtedly been revolutionised by the advent of catalysis. The importance of this field is highlighted by the award of three Nobel Prizes in Chemistry for the development of olefin metathesis processes (2005), transition-metal catalysed cross-coupling (2010), and asymmetric organocatalysis (2021). These reactions benefit from the addition of a small quantity of a tailored catalyst, which can enhance the rate of product formation and impart high levels of selectivity. The latter is fundamentally important, as controlling the spatial arrangement of atoms in a drug is key for potency and reducing side-effects, due to the three-dimensional structural characteristics of biological targets. Moreover, a fluorine atom can bestow several desirable properties on a molecule, which has led to its incorporation into a significant number of agrochemicals, pharmaceuticals, and various functional materials. A convenient method to install fluorine in an organic molecule involves the addition of hydrogen and fluorine atoms to opposite carbon atoms in a carbon-carbon double bond. This hydrofluorination process is a fundamental transformation in organic chemistry that has been studied extensively since its inception. Typical methods to achieve this involve the use of toxic hydrogen fluoride and despite significant advances that have improved the compatibility of this acidic reagent none have enabled control over the spatial arrangement of the fluorine atom giving only racemic mixtures of products. This project seeks to overcome this challenge and provide a general method to perform hydrofluorination reactions using a convenient fluoride source that is relatively non-hazardous and cost-effective with high control over the fluorine atom's spatial arrangement in three dimensions. Moreover, this will be a sustainable catalytic process that avoids toxic and endangered transition metals. The resulting non-racemic fluorine-containing products will be suitable as building blocks to construct new bioactive molecules with clear applications in drug discovery and agrochemistry.
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Key Findings |
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This information can now be found on Gateway to Research (GtR) http://gtr.rcuk.ac.uk
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Potential use in non-academic contexts |
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This information can now be found on Gateway to Research (GtR) http://gtr.rcuk.ac.uk
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Impacts |
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| Description |
This information can now be found on Gateway to Research (GtR) http://gtr.rcuk.ac.uk |
| Summary |
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| Date Materialised |
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Sectors submitted by the Researcher |
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This information can now be found on Gateway to Research (GtR) http://gtr.rcuk.ac.uk
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| Project URL: |
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| Further Information: |
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| Organisation Website: |
http://www.st-and.ac.uk |