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Development of a Cyclization-Functionalization Strategy Based on the Reactivity of Amine-Ligated Boryl Radicals

Project description

New methods for creating high-value amines

Amines serve as fundamental components in pharmaceuticals, agricultural products and advanced materials. Researchers frequently modify them with additional chemical groups to enhance reactivity, binding and solubility. However, standard synthesis methods remain slow and are restrictive in terms of diversity. With the support of the Marie Skłodowska-Curie Actions programme, the CYBO project aims to introduce an innovative strategy that transforms a simple amine, called homoallylic amine, into more complex and valuable structures. The approach uses a borane molecule to trigger a unique chemical reaction that leads to the formation of new cyclic amines. The trigonal planar geometry of the borane molecule offers a versatile platform for the synthesis of amines that could be exploited in drug discovery.

Objective

Functionalized amines are high-value materials with numerous applications as therapeutic agents, agrochemicals and organic materials. The development of strategies for enabling the fast and divergent synthesis of these material can have a positive impact to our ability to discover, manufacture and evolve molecules of high-relevance to our society.

In this proposal we present an innovative approach for the functionalization of homoallylic amines based on their coordination borane (BH3). This will provide access to novel boryl radical species that we will exploit in cyclization-functionalization cascade. This novel reactivity mode will convert the homoallylic amine into a cyclic borylated and functionalized building block that can be further diversified across the sp3 C–B bond by oxidation or Suzuki-Miyaura cross-coupling.

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 high-value and structurally complex drug analogues.

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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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.

€ 217 965,12
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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