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New reactions of sulfoxonium ylides – for safer synthetic chemistry


Project Description

Sulfoxonium ylides offer superior thermal stability over the parent diazo compounds. This advantageous safety feature has attracted interest from process chemists for the synthesis of drug candidates in industry. However, the metal-catalysed reactions of sulfoxonium ylides remains underdeveloped when compared to the vast array of transformations enabled by diazo compounds. It is therefore desirable to fill that gap with transformative methodologies.
Recently, we reported the first metal-catalysed carbon-hydrogen cross-coupling of non-nucleophilic aryl and heteroaryl substrates with α-ketosulfoxonium ylides (Angew. Chem. Int. Ed. 2017, 56, 13117) and the first chemospecific cyclizations of these ylides on aryls and heteroaryls (Angew. Chem. Int. Ed. 2019, 58, 16198).
On the basis of recently published results (Org. Lett. 2019, 21, 296 & J. Org. Chem. 2020, 85, 1126), and by relying the design of new organometallic catalysts, this project will involve the development of new enantioselective reactions of functionalised sulfoxonium ylides that would benefit the pharmaceutical and agrochemical industry.
The project will be led by Dr Christophe Aïssa and is perfectly suited for the training of a postgraduate student who desires to acquire an in-depth knowledge of cutting-edge transition-metal catalysis and organic chemistry. Hence, the selected individual will be prepared to a future career in research in an optimal manner. Our research group is located in the Synthetic Organic Chemistry Laboratory of the University of Liverpool, which offers an ideal environment to learn new techniques and do outstanding science.
Applications are encouraged from highly motivated candidates who have, or expect to have, at least a 2:1 degree or equivalent in Chemistry.
Applications should be made as soon as possible but no later than 30/06/2020, for a start in October. The position will be advertised until recruitment of the appropriate candidate. Informal enquiries are also strongly encouraged and should be addressed to Christophe Aïssa,
Some teaching duties may be required.

Funding Notes

The award will pay full tuition fees and a maintenance grant for 3.5 years (currently £15,285 p.a.) and it is anticipated that the successful candidate will start in October 2020. Applications from candidates meeting the eligibility requirements of the EPSRC are welcome – please refer to the EPSRC website.
Please quote Studentship Reference: CCPR003 in the Finance Section of the Application Form.

References

Angew. Chem. Int. Ed. 2017, 56, 13117
Angew. Chem. Int. Ed. 2019, 58, 16198
Org. Lett. 2019, 21, 296
J. Org. Chem. 2020, 85, 1126

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