The catalytic synthesis of sulfonamide and sulfonimidamide building blocks from simple feedstocks (CSHP CDT)

Sulfur derived functional groups are found in medicinal agents used to treat to broad range of indications. Sulfonamides are most common group, featuring in >10% of medicines. The aza-variants of these groups, such as sulfonimidamides and sulfoximines, are becoming increasingly popular, but their use is still limited by the lack of general synthetic methods. We have developed a series of catalytic processes to target these aza-sulfur functional groups, several of which employ sulfinylamine (R-NSO) reagents. In this project we will develop new catalytic methods that will convert simple feedstock starting materials, such as carboxylic acids, amino acids, alcohols, and amines, used in combination with sulfinylamine reagents, into valuable, complex, sulfonamide and sulfonimidamide building blocks. Both transition metal catalysis and photocatalysis approaches will be explored. The sulfur atom in many of these aza-sulfur functional groups is chiral, and the control of stereochemistry at this centre will also feature. Throughout the project an emphasis will be placed on developing translatable methods, directly relevant for use in discovery chemistry. Within this, we are keen to prepare highly functionalised motifs that can function as multi-use building blocks.

This is a collaborative project with J&J (Janssen).

Key publications:

• Photocatalytic Carboxylate to Sulfinamide Switching Delivers a Divergent Synthesis of Sulfonamides and Sulfonimidamides. (J. Am. Chem. Soc. 2023, 145, 21623)
• Exploiting trans-Sulfinylation for the Synthesis of Diverse N-Alkyl Sulfinamides via Decarboxylative Sulfinamidation. (Angew. Chem. Int. Ed. 2024, e202407970)

Useful links:

• Willis research group

Supervisory team:

• Michael Willis: [email protected] (Oxford)

Further information

The EPSRC Centre for Doctoral Training in Chemical Synthesis for a Healthy Planet (CSHP CDT) is a new EPSRC-funded centre focused on training the next generation of synthetic chemists, developing a sustainable, innovative chemistry culture that equips students to address major emerging and future global challenges in Human Health, Energy & Materials, and Food Security.

We offer a fully-funded four year PhD programme, delivered jointly by the Universities of Oxford and York, comprised of taught courses and a substantive research project. Student cohorts will work together in a 4-month training period at both Oxford and York, before embarking on their main PhD projects. These substantive projects will be industry co-supervised, and based at either the Department of Chemistry in Oxford, or the Green Chemistry Centre of Excellence at York and the associated Department of Chemistry.

This PhD project will primarily be based at the University of Oxford.

The first application deadline is 15^th November 2024. We will continue to receive applications following this deadline, however some of the projects may be filled following the assessment of the first round of applications. We therefore encourage you to submit your application early to ensure that your first-choice project is available. A full list of CSHP CDT projects on offer can be found here.

All project partners recognise the importance of equal participation, progression and success for all. We strive to provide a working, learning, social and living environment that will enable all our staff and students to contribute fully, to flourish and to excel – a place where we can ALL be ourselves.

The Department of Chemistry in Oxford holds an Athena SWAN Silver Award and is committed to supporting equality and diversity for all staff and students. The Department strives to provide a working environment which allows all staff and students to contribute fully, to flourish, and to excel; for more details, see https://www.chem.ox.ac.uk/equality-and-diversity. In particular, we recognise the importance of the equal participation of women at all levels in a subject that has traditionally been male-dominated. We also particularly encourage applications from people who identify as Black, Asian or from a Minority Ethnic background, who are underrepresented in science.

Eligibility Criteria

You must have, or expect to gain, a minimum 2:1 Honours degree or international equivalent in a subject relevant to the proposed PhD project (usually chemistry or chemical engineering, but please get in touch if you think your qualification may be relevant). Enthusiasm for research, the ability to think and work independently, excellent analytical skills and strong verbal and written communication skills are also essential requirements.

How to apply  

For information on how to apply, visit the CSHP CDT website: https://cshp-cdt.chem.ox.ac.uk/apply/how-to-apply.html.

You will need to prepare the following information:  

• 1000-word personal statement, focusing on your interest and experience in your proposed field of research
• Clearly state your 1-2-3 choice of substantive research projects chosen from our list at the end of your personal statement
• Transcripts detailing your university-level qualifications and marks to date
• Three Academic/Professional References: you will be required to submit contact details for 3 referees

The start date of the PhD will be 1^st October 2025.

For more details on the application and selection processes, and for answers to general questions (i.e. funding eligibility, project allocation, etc.) please visit our FAQs section.