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Intermolecular enantioselective amination of unactivated C(sp3)–H bonds

Project description

Exploring alkanes conversion to valuable chemicals

Alkanes, key components of natural gas and by-products of the petrochemical industry, are abundant but challenging to convert due to the inertness of their C(sp3)–H bonds. This makes creating higher-value products from alkanes a significant hurdle. With the support of the Marie Skłodowska-Curie Actions programme, the Rhod-to-N project aims to overcome this challenge by developing rhodium-catalysed methods for selectively aminating unactivated C–H bonds. The project will focus on transforming aryl alkanes into chiral building blocks like β-arylethylamines and α-methylamines, which are valuable for the development of live-saving medicines. With innovative techniques and continuous flow applications, Rhod-to-N promises to revolutionise alkane valorisation, boosting European competitiveness in sustainable chemical production and providing growth opportunities for researchers.

Objective

Alkanes, the principal components of natural gas and widely produced by the petrochemical industry, represent a significant carbon source for chemical synthesis. However, due to the low reactivity of the C(sp3)–H bond, converting alkanes into higher-value products is challenging and remains one of the Holy Grails of chemistry. In this context, transition metal-catalyzed C(sp3)–H bond amination has emerged as a powerful tool for alkane derivatization. However, this transformation is almost exclusively limited to the functionalization of activated C–H bonds, such as those at benzylic positions. Therefore, the development of catalytic systems that enable the exclusive regio- and stereoselective functionalization of unactivated C–H bonds in the presence of more reactive sites would represent a groundbreaking advancement in organic synthesis.

The Rhod-to-N project (intermolecular enantioselective amination of unactivated C(sp3)–H bonds) aims to push these boundaries by discovering efficient enantioselective rhodium-catalyzed methods for the transformation of aryl alkanes into β-arylethylamines and α-methylamines, which serve as privileged chiral building blocks for the development of novel life-saving medicines.

To achieve this ambitious goal the project will focus on accomplishing the following objectives:

1) Development of the intermolecular enantioselective amination of homobenzylic sites.
2) Intermolecular enantioselective amination of terminal methylenes.
3) Continuous flow applications employing reusable catalytic columns.

The successful completion of this project will contribute to the innovative valorization of low-cost aryl alkanes, yielding significant scientific, societal, and economic impacts, and bolstering European competitiveness in the sustainable production of fine chemicals. Additionally, the project will offer substantial growth opportunities to the researcher through high-value scientific and complementary training.

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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

CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE CNRS
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.

€ 226 420,56
Address
RUE MICHEL ANGE 3
75794 PARIS
France

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Ile-de-France Ile-de-France Paris
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