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Reversible Creation of Non-Inherent Reactivity Patterns in Catalytic Organic Synthesis

Objective

Current methods in organic synthesis only enable reactions at the most reactive bonds or at bonds predisposed by specific directing groups. Consequently, many less reactive bonds, including numerous C-H and C-C bonds, cannot be functionalized, enormously limiting the scope of possible transformations. To overcome these limitations, I propose Reverse&Cat, a revolutionary strategy using a novel method to change the reactivity pattern of molecules. This strategy combines the dynamic equilibrium mediated by the first catalyst and a functionalization reaction catalyzed by the second catalyst. The originality of the transformation stems from exploiting three simultaneous processes: (i) the dynamic exchange of one functional group (FG) for another FG that modulates the reactivity of the substrate; (ii) the functionalization of the temporarily activated bond; and (iii) the restoration of the initial FG. In essence, the processes (i) and (iii) – the components of the dynamic equilibrium – realize the novel concept of the temporary creation of non-inherent reactivity of a substrate.
The program is divided in three phases, which will establish the full potential of the strategy. In phase A, I will develop a set of new reactions enabled by the bi-catalytic systems. I will exploit two types of reversible reactions: (1) reversible oxidation of alcohols, which delivers temporarily activated aldehydes/ketones, with the distinct reactivity of their C-H bonds; and (2) reversible retro-hydrofunctionalization of nitriles or their analogues, which delivers temporarily activated alkenes, containing allylic C-H and C=C bonds. In phase B, I will conduct detailed mechanistic studies to gain the mechanistic understanding and enable further rational development. In phase C, I will establish the utility of this new strategy in practical organic synthesis. Overall, the strategy will open a new dimension of reactivity, with prospective applications in production of fine-chemicals and materials.

Host institution

CENTRE INTERNATIONAL DE RECHERCHE AUX FRONTIERES DE LA CHIMIE FONDATION
Net EU contribution
€ 519 800,00
Address
Allee G Monge 8
67000 Strasbourg
France

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Region
Grand Est Alsace Bas-Rhin
Activity type
Research Organisations
Non-EU contribution
€ 0,00

Beneficiaries (2)

CENTRE INTERNATIONAL DE RECHERCHE AUX FRONTIERES DE LA CHIMIE FONDATION
France
Net EU contribution
€ 519 800,00
Address
Allee G Monge 8
67000 Strasbourg

See on map

Region
Grand Est Alsace Bas-Rhin
Activity type
Research Organisations
Non-EU contribution
€ 0,00
Third-party

Legal entity other than a subcontractor which is affiliated or legally linked to a participant. The entity carries out work under the conditions laid down in the Grant Agreement, supplies goods or provides services for the action, but did not sign the Grant Agreement. A third party abides by the rules applicable to its related participant under the Grant Agreement with regard to eligibility of costs and control of expenditure.

UNIVERSITE DE STRASBOURG
France
Net EU contribution
€ 1 211 450,00
Address
Rue Blaise Pascal 4
67081 Strasbourg

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Region
Grand Est Alsace Bas-Rhin
Activity type
Higher or Secondary Education Establishments
Non-EU contribution
€ 0,00