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A strategy for the deconstruction and functionalization of saturated nitrogen heterocycles using boryl radical reactivity

Project description

Cyclical amine functionalisation

Functionalising cyclic amines, which are found in natural products and therapeutics, has long been a challenge in chemistry. Traditional methods rely on replacing C–H bonds with new functionalities, limiting possibilities. Supported by the Marie Skłodowska-Curie Actions programme, the DECONSTRUCT project will introduce a radical deconstruction approach. By coordinating amines with BH3, the team activates boryl radicals that can fragment and undergo radical functionalisation. This process transforms cyclic amines into acyclic derivatives and diversifies their potential applications. Led by the Leonori group at RWTH Aachen University, the project not only pushes the boundaries of chemical synthesis but also offers valuable training for the next generation of researchers in this cutting-edge field.

Objective

Cyclic amines are high-value molecules found in both natural products (alkaloids, proline…) and small-molecule therapeutics. The development of strategies for the selective and divergent functionalization of these derivatives can provide new opportunities for the discovery and evolution of materials of high relevance to our society.

In general, cyclic amines are functionalised by introduction of new functionalities in place of C–H bonds. In this work we propose a fundamentally novel way to modify amines by means of radical deconstruction and tandem functionalization. This strategy will convert these cyclic materials into acyclic ones and further introduce additional substituents.

The chemistry will involve amine activation by simple coordination with BH3. This will enable access to a boryl radical that can undergo e fast fragmentation followed by a radical functionalization process.

Overall, this strategy will constitute a divergent platform for the diversification of high-value amines and also a novel retrosynthetic tactic for the preparation of acyclic derivatives.

This research squarely fits within the expertise of the Leonori group in the generation and use of boryl radicals in synthesis and catalysis.

The completion of such an innovative and ambitious project at RWTH Aachen University will be facilitated by generating, transferring, sharing and disseminating knowledge, and will enhance the Researcher future career following the training plan envisioned.

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Programme(s)

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Topic(s)

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Funding Scheme

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HORIZON-TMA-MSCA-PF-EF - HORIZON TMA MSCA Postdoctoral Fellowships - European Fellowships

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Call for proposal

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(opens in new window) HORIZON-MSCA-2024-PF-01

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Coordinator

RHEINISCH-WESTFAELISCHE TECHNISCHE HOCHSCHULE AACHEN
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.

€ 202 125,12
Address
TEMPLERGRABEN 55
52062 Aachen
Germany

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Region
Nordrhein-Westfalen Köln Städteregion Aachen
Activity type
Higher or Secondary Education Establishments
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Total cost

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