Dr. Balázs L. Tóth

Prof. Arjan Kleij

Dual Co/Photoredox Catalysis for the Synthesis of Fluorine-Containing Skipped Dienes Featuring a Quaternary Carbon Stereocenter

Balázs L. Tóth joined the team of Arjan W. Kleij as a MSCA Fellow in 2022. He started his chemical research career in the group of Zoltán Novák at Eötvös Loránd University (ELTE) Budapest, Hungary where he gained experience in C-H activation, synthesis of bimetallic palladium complexes and transition metal catalysis. In 2016 he did a half-year internship at the University of Regensburg, in Germany, where he studied photoredox transformations under the supervision of Burkhard König. In 2020 he defended his PhD work at ELTE which explored the application of hypervalent iodine reagents in direct fluoroalkylation and fluoroalkenylation reactions. In the following year he joined the group of Martín Fañanás Mastral at CiQUS, in Santiago de Compostela, Spain as a postdoctoral researcher. He investigated Pd/Cu cooperative catalysis, allylic chemistry and carried out photocatalytic C-H activation of light alkanes. Currently he is searching for reactivity between electrophilic hydrofluoroolefins and carbon-based nucleophiles prepared via photoredox-controlled ‘Umpolung’ reduction of electrophilic allyl carbonates. Besides chemistry, he enjoys playing basketball, learning computer-based programming languages, and hiking in the mountains.

From 15/06/2022 to

14/06/2024

FUSE

Fluorine-containing functional groups have become of crucial importance for medicinal and agrochemical applications. The
incorporation of these moieties into molecular structures allows for significant opportunities to take advantage of
bioisosterism as well as to fine-tune the chemical or pharmacological properties of a desired molecule. The objective of the
FUSE project is to pioneer a novel approach for the preparation of fluorinated and chiral skipped dienes bearing a
quaternary carbon stereocenter. Developing methodologies for these elusive compounds allows for a wide range of synthetic
post-transformations and they thus serve as valuable building blocks in synthetic chemistry and pharmaceutical development
programs. The project will expand the chemical space of hydrofluoroolefins (HFOs) and utilize these fourth-generation
refrigerants as readily available and inexpensive starting materials. To achieve the challenging targets, a mild, visible-light
photoredox based dual catalytic approach is utilized using earth-abundant (cobalt) first-row transitional metal catalysis. As
such, the replacement of the typically hazardous metal reagents utilized in the state of the art and minimizing chemical waste
is forecasted. The proposed programme will be carried out in close cooperation with an industrial partner in order to provide
a new flow strategy for constructing these skipped fluorodiene scaffolds. This ambitious and innovative project will contribute
to propagate the sustainability and reinforce the application potential of HFOs for academic and industrial applications. The
project merges multidisciplinary aspects with intersectorial knowledge transfer, enabling the transition to more sustainable
development in the fine chemical and pharmaceutical sector.

This project has received funding from the European Union’s Horizon 2020 research and innovation program under grant agreement 101026029