Descrizione del progetto
Un percorso senza alogeni per la costruzione e la decostruzione reversibili di dialogenuri
I composti polialogenati, composti di carbonio costituiti da più di un atomo di alogeno, sono comunemente usati in farmaceutica e in agricoltura e fungono anche da promettenti elementi costitutivi nell’industria chimica. La maggior parte delle reazioni di alogenazione, tuttavia, prevede l’uso di reagenti pericolosi quali il cloro (Cl2) e il bromo biatomico (Br2). Questa sfida di lunga data può essere affrontata mediante la catalisi dello shuttle. Questa potente nuova strategia trasferisce in modo reversibile una frazione chimica tra due molecole per costruire e decostruire composti senza coinvolgere reagenti pericolosi. Il progetto HaloCat, finanziato dall’UE, utilizzerà la catalisi dello shuttle per ottenere l’interconversione reversibile di 1,2-dialogenuri e alcheni senza utilizzare il Br2 o il Cl2. Un altro obiettivo sarà quello di realizzare il trasferimento enantioselettivo di Br2 tra 1,2-dialogenuri e alcheni.
Obiettivo
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.
Campo scientifico
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Meccanismo di finanziamento
MSCA-IF-EF-ST - Standard EFCoordinatore
8092 Zuerich
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