New advances in photoredox catalysis : applications in radical chemistry synthesis and dual catalysis

Abstract : Visible-light photoredox catalysis has emerged as a very powerful strategy to generate radical species replacing more and more tin-mediated or stoichiometric redox methodologies. The main objective of the research described in this Ph. D. thesis is to develop new synthetic methodologies in radical and organometallic chemistry, and merge them in a dual catalysis process for the preparation of elaborated molecular building blocks. In a first study, we report a photocatalytic alternative of Barton-McCombie deoxygenation based on a visible-light photoreduction of O-thiocarbamates derived from secondary and tertiary alcohols. A mechanistic investigation is presented based on fluorescence quenching and cyclic voltammetry experiments. In a second study, a challenging method of generation of unstabilized alkyl radicals by photooxidation of borate salts or hypervalent silicon species is reported. These radicals are trapped by free radical scavengers or engaged in a photoredox/nickel dual catalysis.
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Ludwig Chenneberg. New advances in photoredox catalysis : applications in radical chemistry synthesis and dual catalysis. Organic chemistry. Université Pierre et Marie Curie - Paris VI, 2016. English. ⟨NNT : 2016PA066305⟩. ⟨tel-01467135⟩

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