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Sulfonium salts as pseudohalide electrophiles for cross-coupling having improved tractability, orthogonality, stability and environmental profile

  • Full or part time
  • Application Deadline
    Sunday, February 09, 2020
  • Funded PhD Project (European/UK Students Only)
    Funded PhD Project (European/UK Students Only)

Project Description

The University of Bath is inviting applications for the following PhD project supervised by Dr Simon Lewis https://researchportal.bath.ac.uk/en/persons/simon-lewis in the Department of Chemistry.

Formation of C-C and C-X bonds using cross-coupling, catalysed by palladium or other transition metals, has become a mainstay of organic synthesis. Whereas a range of choices have been extensively investigated for the nucleophilic cross-coupling partner (organoboron, organotin, organozinc, organomagnesium, copper acetylides, etc.), the choice of electrophilic coupling partner has been comparatively underexplored. The classical use of organohalides to fulfil this role has been augmented by the use of pseudohalide coupling partners such as triflates and tosylates, but sulfonium salts are an underutilised alternative. We recently reported the preparation of sulfonium salts of azulene, an unusual bicyclic aromatic compound with applications in fluorescence sensing and organic electronics. Whereas azulene halides are unstable and difficult to purify, azulenesulfonium salts are stable crystalline salts that engage in cross-couplings such as Suzuki-Miyaura reactions. We synthesised the azulenesulfonium salts by means of a so-called “interrupted Pummerer” reaction that simply requires a sulfoxide and activating agent.

We now wish to explore the applicability of this synthesis of sulfonium salts to substrates other than azulene, with a view to exploiting sulfonium salt cross-coupling in cases where the classical halide coupling partners are known to be problematic. This project will involve primarily synthetic organic chemistry, with extensive compound characterisation by NMR, and x-ray crystallography, as well as mechanistic studies using our Dynamic Reaction Monitoring flow-NMR facility. There is also scope for the student to undertake computational modelling of the reactions under study.

Candidate requirements:

Applicants should hold, or expect to receive, a First Class or good Upper Second Class Honours degree in Chemistry, or the equivalent from an overseas university. A master’s level qualification would also be advantageous.

Enquiries and applications:

Informal enquiries are welcomed and should be directed to .

Formal applications should be made via the University of Bath’s online application form for a PhD in Chemistry:
https://samis.bath.ac.uk/urd/sits.urd/run/siw_ipp_lgn.login?process=siw_ipp_app&code1=RDUCH-FP01&code2=0014

More information about applying for a PhD at Bath may be found here:
http://www.bath.ac.uk/guides/how-to-apply-for-doctoral-study/

Anticipated start date: 28 September 2020.

Funding Notes

Research Council funding is available for an excellent UK or EU student who has been ordinarily resident in the UK since September 2017. For more information on eligibility: View Website.

Funding will cover UK/EU tuition fees, maintenance at the UKRI doctoral stipend rate (£15,009 per annum tax-free in 2019/20, increasing annually in line with the GDP inflator) and a training support grant (£1,000 per annum) for a period of up to 3.5 years.

We also welcome all-year-round applications from self-funded candidates and candidates who can source their own funding.

References

Lewis et al., Angew. Chem. Int. Edn. 2016, 55, 2564. DOI:10.1002/anie.201510666

How good is research at University of Bath in Chemistry?

FTE Category A staff submitted: 33.10

Research output data provided by the Research Excellence Framework (REF)

Click here to see the results for all UK universities

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