Project description
Novel approach could yield single-step aziridine ring-opening and functionalisation
Beta-functionalised amines are essential building blocks in pharmaceuticals and agrochemicals, yet synthesising them efficiently remains challenging. Aziridines – highly reactive nitrogen-containing rings – are promising starting materials but current methods for opening them are limited to pre-activation of aziridines and there are no methods for their direct functionalisation into beta-amines. With the support of the Marie Skłodowska-Curie Actions programme, the AZIRIDINE project aims to change this with a new approach based on boryl radical chemistry, enabling direct, single-step ring-opening and functionalisation without pre-activation. This strategy could establish a powerful new synthetic platform for rapidly accessing medicinally relevant molecules and late-stage diversification of bioactive drug scaffolds.
Objective
β-Functionalized amines are privileged motifs in pharmaceuticals, and agrochemicals, yet their synthesis typically requires lengthy & challenging routes. Aziridines represent attractive starting points, but current ring-opening strategies are restricted to pre-activated substrates bearing strong electron-withdrawing groups, which limits their synthetic utility. No general methods exist for the direct functionalization of unprotected or N-alkyl aziridines into β-amines.
This project introduces a new approach that harnesses boryl radical chemistry to directly deconstruct aziridines. Coordination of BH₃ to the aziridine will enable generation of aziridine-bound boryl radicals, which undergo selective β-scission to produce β-aminoalkyl radicals. These intermediates will then be intercepted by radical acceptors to deliver a broad range of β-functionalized amines in a single step.
The methodology will progress in two stages: (1) development of photocatalytic ring-opening processes and divergent radical functionalizations using many SOMOphiles, and (2) integration with nickel catalysis to achieve cross-couplings with aryl, alkyl, and acyl partners. Mechanistic elucidation by spectroscopy, actinometry, and photolysis will underpin the design and guide reaction development.
This strategy establishes the first general platform for aziridine ring-opening and functionalization without pre-activation, opening a new retrosynthetic paradigm for the synthesis of β-amines. Beyond methodological innovation, it provides a blueprint for the late-stage diversification of bioactive scaffolds and creates powerful shortcuts to molecules of direct medicinal relevance.
Completion of this innovative and ambitious project at RWTH Aachen University will be supported by comprehensive training, knowledge transfer, and dissemination, enhancing the Researcher’s career trajectory and equipping him with unique expertise at the interface of synthesis, radical chemistry, and photochemistry.
Fields of science (EuroSciVoc)
CORDIS classifies projects with EuroSciVoc, a multilingual taxonomy of fields of science, through a semi-automatic process based on NLP techniques. See: The European Science Vocabulary.
CORDIS classifies projects with EuroSciVoc, a multilingual taxonomy of fields of science, through a semi-automatic process based on NLP techniques. See: The European Science Vocabulary.
- natural sciences chemical sciences inorganic chemistry transition metals
- natural sciences chemical sciences physical chemistry photochemistry
- natural sciences chemical sciences catalysis
- natural sciences chemical sciences organic chemistry amines
- natural sciences physical sciences optics spectroscopy
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Project’s keywords as indicated by the project coordinator. Not to be confused with the EuroSciVoc taxonomy (Fields of science)
Project’s keywords as indicated by the project coordinator. Not to be confused with the EuroSciVoc taxonomy (Fields of science)
Programme(s)
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Multi-annual funding programmes that define the EU’s priorities for research and innovation.
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HORIZON.1.2 - Marie Skłodowska-Curie Actions (MSCA)
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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.
HORIZON-TMA-MSCA-PF-EF - HORIZON TMA MSCA Postdoctoral Fellowships - European Fellowships
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(opens in new window) HORIZON-MSCA-2025-PF
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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.
52062 Aachen
Germany
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