Novel catalytic hydrosilane mediated reduction reactions

Stoll, Emma (2021) Novel catalytic hydrosilane mediated reduction reactions. PhD thesis, University of Nottingham.

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Abstract

This thesis starts with an introduction to the relevant organosilicon and reduction chemistry concepts that underpin the chemistry that is explored in later chapters. In particular, hyperconjugation, relevant organosilicon reagent classes and reduction of carbonyl containing compounds are explored.

Chapter one describes a reductive amination reaction with carboxylic acids in lieu of lower oxidation state alternatives such as aldehydes or alkyl halides. A two-step reaction process is described, whereby the dual reactivity of phenylsilane is exploited in an initial amidation followed by a zinc acetate-catalysed amide reduction. The reaction is applicable to a wide range of substrates and several potential applications have been explored, as well as mechanistic studies.

Chapter two builds on the utility of the novel zinc acetate / phenylsilane reduction system for the reduction of carboxylic acids to the corresponding alcohols. However, this time employing the use of zinc acetate and N-methyl morpholine in a dual catalytic system. The protocol is applicable to a wide range of substrates and proceeds via activation using hydrosilanes. Mechanistic studies have also been undertaken to gain insights into the reaction mechanism.

Item Type: Thesis (University of Nottingham only) (PhD)
Supervisors: Denton, Ross M
Keywords: Novel catalytic hydrosilane
Subjects: Q Science > QD Chemistry > QD241 Organic chemistry
Faculties/Schools: UK Campuses > Faculty of Science > School of Chemistry
Item ID: 64543
Depositing User: Stoll, Emma
Date Deposited: 31 Jul 2021 04:40
Last Modified: 31 Jul 2021 04:40
URI: http://eprints.nottingham.ac.uk/id/eprint/64543

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