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Transient Directing Group Mediated C-H Functionalisation


   School of Chemistry

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  Dr Tom Storr  No more applications being accepted  Self-Funded PhD Students Only

About the Project

Transition metal catalysed C-H bond functionalisation chemistry has, over the last two decades, come to represent the state-of-the-art of synthetic transformations. The ideals of rapid, selective and atom economic chemical manipulations without the prerequisite for pre-activated substrates ties in directly with the principles of green chemistry and sustainable chemistry. This PhD programme in the Storr Group aims to develop a holistic approach to C-H functionalisation methodology, by employing a flexible approach with the ability to select a ligand (Transient Directing Group, TDG) which has the structural flexibility to be fine-tuned to accommodate specific substrates and support multiple transition metal catalysts. This is highly appealing to the synthetic community.

A generalised structure of a TDG contains two important components 1) a substrate binding moiety and 2) the catalyst binding moiety. Considering the catalytic cycle, only the substrate binding of the two binding functionalities needs to be reversible, hence, supramolecular interactions lend themselves to mild reversible binding. Supramolecular interactions (electrostatic, hydrogen bonding, pi-pi interactions, etc.) and host/guest chemistry (calixarenes, cucurbiturils, cyclodextrins, etc.) will be used as the transiently interacting component within the TDG ligand designs. Application of this approach to C-H bond arylation, alkenylation, halogenation, amination and oxygenation reactions will deliver novel methodologies for rapid synthetic elaboration of both C(sp2)-H and C(sp3)-H bonds.

This project unites the two currently disparate fields of TDG mediated C-H functionalisation chemistry and supramolecular host/guest recognition and ties them together in a novel ligand design with great synthetic potential. The proposed work aligns with a number of the synthetic chemistry interest areas, specifically aspects of innovative synthetic organic chemistry with applications to heterocycle elaboration, in addition to C-H bond functionalisation methodology targeted at protein modification. The PhD candidate will be provided with an excellent training opportunity and have the opportunity to contribute scientific findings to the fields of catalysis, synthetic organic chemistry, supramolecular chemistry and chemical biology.


Funding Notes

This PhD project is offered on a self-funding basis. It is open to applicants with funding or those applying to funding sources. Details of tuition fees can be found at https://www.uea.ac.uk/about/university-information/finance-and-procurement/finance-information-for-students/tuition-fees
A bench fee is also payable on top of the tuition fee to cover specialist equipment or laboratory costs required for the research. Applicants should contact the primary supervisor for further information about the fee associated with the project.

References

i) S. Rej, A. Das and N. Chatani, Coord. Chem. Rev., 2021, 431, 2136832
ii) L. Guillemard, N. Kaplaneris, L. Ackermann and M. J. Johansson, Nat. Rev. Chem., 2021,5, 522
iii) R. Ali and R. Siddiqui, Adv. Synth. Cat., 2021, 363, 1290
iv) Ed. –I.T. Horváth, Chem. Rev., 2018, 118, 369
v) K. N. Ganesh, D. Zhang, S. J. Miller, K. Rossen, P. J. Chirik, M. C. Kozlowski, J. B. Zimmerman, B. W. Brooks, P. E. Savage, D. T. Allen and A.M. Voutchkova-Kostal, Environ. Sci. Technol. Lett. 2021, 8,487
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