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Development of Triptycene-Based New Hypervalent Iodine Reagents for Selective Organic Synthesis

Project description

Novel methodology for selective organic synthesis

Industrial processes necessitate chemical compounds that exhibit great chemo-, regio- and stereoselectivity. Selectivity is achieved through covalent interactions of metals or non-covalent interactions such as hydrogen bonding, halogen bonding or ion pairing involving organocatalysts or enzyme catalysts. The EU-funded Triplod project proposes to use the highly promising triptycenes as a scaffold for the synthesis of iodine-based reagents. Researchers will exploit the rigidity of these aromatic hydrocarbons and their potential to form non-covalent interactions. The Triplod methodology can be employed in automated flow synthesis, opening new directions for the generation of polymer-based reagents and contributing towards new industrial protocols.

Objective

The challenge of achieving high selectivities (chemo/regio/stereoselectivity) in organic transformations is still very high. Selectivities are achieved through either covalent interactions involving metals or non-covalent interactions such as hydrogen bonding, halogen bonding or ion pairing involving organocatalysts or enzyme catalysts. Triptycenes are highly promising structures due to their rigidity, internal free volume, electron rich cavities, three aromatic rings opened for π-stacking interactions and the possibility of atropisomerism. We want to exploit their potential of non-covalent interactions in chemo-, regio- and stereoselective reactions by using triptycene scaffolds for the synthesis of iodine-based reagents. The proposed research will focus in utilization of internal free volume for selectivity in reactions to explore selectivity through π-interaction. This process will open up new directions by focusing on the following objectives: (a) synthesis of different iodotriptycenes; (b) oxidation of iodotriptycene to iodine(III) derivatives including polymer-based reagents; (c) development of chiral triptycene-based iodine(III) derivatives; (d) application of the methodology in the flow synthesis of target molecules and (e) training through research and career development of incoming post-doctoral fellow. The proposed methodology has the capacity to make a sound impact on the scientific community, and to change existing protocols in industry. The MSC Fellowship will provide the post-doctoral fellow to strengthen scientific knowledge and enrich skills, innovative ideas, managing skills and to establish himself as an international scientist.

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Topic(s)

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Funding Scheme

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MSCA-IF-EF-ST - Standard EF

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Call for proposal

Procedure for inviting applicants to submit project proposals, with the aim of receiving EU funding.

(opens in new window) H2020-MSCA-IF-2017

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Coordinator

CARDIFF UNIVERSITY
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.

€ 183 454,80
Address
RESEARCH SERVICES C/O MAIN BUILDING
CF10 3AT CARDIFF
United Kingdom

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Region
Wales East Wales Cardiff and Vale of Glamorgan
Activity type
Higher or Secondary Education Establishments
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Total cost

The total costs incurred by this organisation to participate in the project, including direct and indirect costs. This amount is a subset of the overall project budget.

€ 183 454,80
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