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Exploring the use of enabling technologies for synthetic organic chemistry

Sagatov, Yerbol 2017. Exploring the use of enabling technologies for synthetic organic chemistry. MPhil Thesis, Cardiff University.
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Abstract

The two-step preparation of triazenes from commercially available anilines using a continuous-flow technique was demonstrated (Scheme 1). Furthermore, once conditions for the production were optimised, these conditions were applied on a variety of substrates, including both anilines and secondary amines. Finally, the scalability of the procedure was demonstrated during an 18-hour operation. Secondly, the electrophilic fluorination of a variety of activated methylene compounds was performed mechanochemically (Scheme 2). The efficiency of the mechanochemical fluorination is demonstrated by the following outcomes: the increase of the product yield for some examples, reduction of reaction time and/or more selective production of mono- versus difluorinated compounds (in the presence of a LAG or a base) compared to solution-based reactions. Finally, the multistep mechanochemical synthesis of a fluorinated pyrazolone was conducted. The electrophilic fluorination of a ß-ketoester was performed followed by a cyclisation with phenylhydrazine to form a pyrazolone. Alternatively, the reaction order could be reversed, first forming the pyrazolone followed by the electrophilic fluorination (Scheme 3). The optimisation of these reactions was made separately and the products were obtained in excellent yields.

Item Type: Thesis (MPhil)
Status: Unpublished
Schools: Chemistry
Subjects: Q Science > QD Chemistry
Date of First Compliant Deposit: 17 August 2017
Last Modified: 24 Aug 2018 01:30
URI: http://orca-mwe.cf.ac.uk/id/eprint/103747

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