Descripción del proyecto
Una ruta sin halógenos para la síntesis y la degradación reversible de dihaluros
Los compuestos polihalogenados, compuestos de carbono que presentan más de un átomo de halógeno, no solo se emplean comúnmente en la industria farmacéutica y en la agricultura, sino que además constituyen componentes básicos prometedores para la industria química. Con todo, la mayoría de las reacciones de halogenación implican el uso de reactivos peligrosos como el dicloro (Cl2) y el dibromo (Br2). Este reto inveterado puede abordarse mediante la catálisis de lanzadera. Esta nueva y potente estrategia transfiere de forma reversible un grupo químico entre dos moléculas para sintetizar o degradar compuestos sin necesidad de utilizar reactivos peligrosos. El proyecto financiado con fondos europeos HaloCat empleará la catálisis de lanzadera para lograr la interconversión reversible de 1,2-dihaluros y alquenos sin utilizar Br2 o Cl2. Otro objetivo será realizar la transferencia enantioselectiva de Br2 entre 1,2-dihaluros y alquenos.
Objetivo
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.
Ámbito científico
Programa(s)
Régimen de financiación
MSCA-IF-EF-ST - Standard EFCoordinador
8092 Zuerich
Suiza