Novel bifunctional HAT catalysts for site-divergent C-H functionalizations mediated by photoredox catalysis

Información del proyecto

BICACH

Identificador del acuerdo de subvención: 838108

DOI

10.3030/838108

Proyecto finalizado el 31 Enero 2020

Fecha de la firma de la CE 8 Abril 2019

Fecha de inicio 1 Mayo 2019

Fecha de finalización 30 Abril 2021

Financiado con arreglo a

• EXCELLENT SCIENCE - Marie Skłodowska-Curie Actions

Coste total

€ 162 806,40

Aportación de la UE

€ 162 806,40

Coordinado por

UNIVERSITAET REGENSBURG
Germany

Periodic Reporting for period 1 - BICACH (Novel bifunctional HAT catalysts for site-divergent C-H functionalizations mediated by photoredox catalysis)

Período documentado: 2019-05-01 hasta 2021-04-30

Resumen del contexto y de los objetivos generales del proyecto

Alkanes are the major components of natural gas and oil which are abundantly produced by the petrochemical industry. They are almost exclusively used as a source of energy following their combustion which can be considered as a waste of a carbon-based feedstock. From the organic chemist’s point of view, alkanes indeed represent a major carbon pool for chemical synthesis which remains poorly explored. To date, the elaboration of complex organic molecules heavily relies on the introduction and manipulation of functional groups, typically carbon-oxygen or carbon-halogen bonds. In this regard, the direct functionalization of aliphatic carbon-hydrogen (C-H) bonds, the most abundant moiety within alkanes, represents a more ideal approach to access molecular complexity. However, there are two major hurdles toward he application of this strategy. First, alkane C-H bonds are very difficult to activate. However, if one can overcome this lack of reactivity, it should then face a daunting selectivity issue: how to activate selectively one single C-H bond within an alkane backbone harnessing many almost identical C-H bonds?

The development of chemical processes enabling the selective conversion of cheap and abundant alkanes into high-value chemicals is one of the Holy grail in organic synthesis. Such endeavour would strongly benefit our society 1) By reducing the amount of chemical waste to access valuable chemical products; 2) By enabling the synthesis of new chemicals with unprecedented properties.

The main objective of this project was to develop a library of small molecules enabling the selective functionalization of alkane through catalytic processes using visible light as a renewable source of energy.

Trabajo realizado desde el comienzo del proyecto hasta el final del período abarcado por el informe y los principales resultados hasta la fecha

Indoles are prevalent motifs in bioactive natural products and pharmaceuticals. Therefore, the development of methods for the synthesis of functionalized of indoles under mild conditions is an important task in synthetic chemistry. In this respect, catalytic transformations enabling the direct functionalization of indole C-H bonds are particularly valuable because they afford complex indole structures with an excellent step and atom-economy. During the BICACH project, we developed a catalytic process to access a range of relevant indoles through selective C-H functionalization. This process is mediated by visible light as a renewable source of energy.

Avances que van más allá del estado de la técnica e impacto potencial esperado (incluida la repercusión socioeconómica y las implicaciones sociales más amplias del proyecto hasta la fecha)

We developed a photocatalytic C-H functionalization strategy mediated by visible light that provides an efficient access to a variety of novel relevant polycyclic indoles. The reaction is scalable and the indole products can be further used as versatile synthetic intermediates to access other important scaffolds such as pyrroloindoles and (pyrrolo)indolines. We expect this methodology to find a widespread use in the synthesis of indole-containing natural products and bioactive compounds. Given the diversity of bioactive profiles amongst indole containing molecules, this project could have wider societal implications through the development of novel medicines.

Synthesis of functionalized indoles by C-H alkylation