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Elemental Halogen-Free Reversible Construction and Deconstruction of 1,2-Dihalides via Shuttle Catalysis

Project description

A halogen-free route to the reversible construction and deconstruction of dihalides

Polyhalogen compounds, carbon compounds that have more than one halogen atom, are commonly used in pharmaceutics and agriculture, and they also serve as promising building blocks in the chemical industry. Most halogenation reactions, however, involve the use of hazardous reagents such as dichlorine (Cl2) and diatomic bromine (Br2). This long-standing challenge can be addressed by shuttle catalysis. This powerful new strategy reversibly transfers a chemical moiety between two molecules to construct and deconstruct compounds without involving hazardous reagents. The EU-funded HaloCat project will employ shuttle catalysis to achieve reversible interconversion of 1,2-dihalides and alkenes without using Br2 or Cl2. Another goal will be to realise the enantioselective Br2 transfer between 1,2-dihalides and alkenes.

Objective

Multi-halogenated compounds play a significant role in our daily life, as they are not only widely used as materials, pharmaceuticals, and agrochemicals but also serve as practical and indispensable building blocks in the chemical industry. However, most of the existing halogenating protocols suffer from safety risks and harsh reaction conditions caused by toxic and corrosive halogenating reagents (Cl2, Br2). Moreover, the enantioselective 1,2-dihalogenation of alkenes remains an unmet challenge. Besides, practical approaches to the versatile 1,2-bromofluorine-containing building blocks are exceedingly rare. Recently, the shuttle catalysis strategy, which reversibly transfers a chemical moiety between two molecules to construct and deconstruct compounds without handling hazardous reagents, is emerging as a potential strategy to tackle these long-standing challenges. This proposal aims to achieve the shuttle catalysis enabled reversible interconversion of 1,2-dihalides and alkenes/alkynes without using or releasing hazardous chemicals (e.g. Br2, Cl2, and BrF) under mild conditions. The first part is devoted to developing the reversible interconversion between 1,2-dihalides and alkenes. The second part aims to realize the enantioselective Br2 transfer between 1,2-dihalides and alkenes. The last part proposes to develop the unprecedented formal transfer 1,2-bromofluorination of alkenes via a unique self-correcting mechanism. The world-leading research environment of ETH Zurich combined with Prof. Morandi’s unrivaled scientific expertise on shuttle catalysis and my excellent knowledge of asymmetric catalysis offer the best combination to achieve the proposed research. This fellowship will dramatically improve my knowledge and competences, helping me launch my independent career. With promising preliminary results demonstrating the project’s feasibility, the proposed work will significantly contribute to the research excellence and sustainable development of the EU.

Coordinator

EIDGENOESSISCHE TECHNISCHE HOCHSCHULE ZUERICH
Net EU contribution
€ 203 149,44
Address
Raemistrasse 101
8092 Zuerich
Switzerland

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Region
Schweiz/Suisse/Svizzera Zürich Zürich
Activity type
Higher or Secondary Education Establishments
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Total cost
€ 203 149,44