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Developing heterocylic sulfinates as general coupling partners in transition metal catalysed processes

Objective

This project focuses on the development of heterocylic sulfinates as general coupling partners in transition metal catalyzed processes, through a desulfinative coupling process that has already shown promising results. Previously, aryl boronic acids, and related boronates, are some of the most versatile and widely used reagents available to synthetic chemists. However, their use is limited due to the low efficiency, poor stability and difficulty in preparation of many heterocycle-derived boronic acids. The Willis laboratory in Oxford has been exploring alternatives to heterocyclic boronic acids in coupling processes, and has recently established that pyridine sulfinates are excellent coupling partners in palladium-catalyzed coupling reactions with aryl and heteroaryl halides. Very recently they have shown that this chemistry can be extended to the use of alternative heterocycles, such as pyrimidine, pyrazine, pyridazine, imidazole, pyrazole and indazole cores. The use of these heterocycle sufinates addresses many of the limitations of the corresponding boronic acids (ease of preparation and use, storage stability and reactive efficiency). The remarkable utility of heteroaryl sulfinates in coupling with (hetero)aryl halides suggests that the chemistry could be extended to tackle several remaining challenges associated with heterocycle functionalization, specifically elaborating heterocycle cores with small (cyclic)alkyl substituents, and introducing diverse N- and O-based nucleophile coupling partners. Protected versions of these sulfinates, so called masked sulfinates, will also be developed. These three areas of investigation encompass the scope of the proposal.

Keywords

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Programme(s)

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Topic(s)

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Funding Scheme

Funding scheme (or “Type of Action”) inside a programme with common features. It specifies: the scope of what is funded; the reimbursement rate; specific evaluation criteria to qualify for funding; and the use of simplified forms of costs like lump sums.

MSCA-IF - Marie Skłodowska-Curie Individual Fellowships (IF)

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Call for proposal

Procedure for inviting applicants to submit project proposals, with the aim of receiving EU funding.

(opens in new window) H2020-MSCA-IF-2017

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Coordinator

THE CHANCELLOR, MASTERS AND SCHOLARS OF THE UNIVERSITY OF OXFORD
Net EU contribution

Net EU financial contribution. The sum of money that the participant receives, deducted by the EU contribution to its linked third party. It considers the distribution of the EU financial contribution between direct beneficiaries of the project and other types of participants, like third-party participants.

€ 183 454,80
Address
WELLINGTON SQUARE UNIVERSITY OFFICES
OX1 2JD Oxford
United Kingdom

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Region
South East (England) Berkshire, Buckinghamshire and Oxfordshire Oxfordshire
Activity type
Higher or Secondary Education Establishments
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Total cost

The total costs incurred by this organisation to participate in the project, including direct and indirect costs. This amount is a subset of the overall project budget.

€ 183 454,80
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