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## Development of a synthesis procedure for selected trifluoroorganoborates

### Błażej Ogonowski

#### Abstract

Introduction: Trifluoroorganoborates are organo-boron compounds containing in their structure an anion of general formula [R-BF3] - and a cation (usually K +). They are compounds that, unlike other derivatives of organo-borane compounds (eg esters) are easy to maintain, do not absorb moisture and are easy to purify. These compounds are used in organic synthesis, especially in the Suzuki-Miyaura reaction and in photocatalytic reactions. The purpose of the work was the synthesis and optimization of the synthesis of selected trifluoroorganoborates: potassium 3-phenylprop-2-enyltrifluoroborate, potassium 3-(1H-pyrazol-1-yl)prop-1-enyltrifluoroborate and potassium 3-allyl-2,4-difluorophenyltrifluoroborate. Results and discussion: Potassium 3-phenylprop-2-enyl-trifluoroborate was obtained in a complex process consisting of lithiation of allylbenzene, reaction of the obtained lithium derivative with B(OEt)3 and hydrolysis in aqueous KHF2 solution. Potassium 3-(1H-pyrazol-1-yl)prop-1-enyltrifluoroborate was not obtained. The synthesis process was completed at the stage of optimization of the 1-propargylpyrazole preparation procedure, because the hydroboration reaction to form a B-C bond did not give a result. The conditions for the synthesis of 1-propargylpyrazole were investigated: the process for the choice of the base and the molar ratio of substrates needed to carry out the reaction were described. Potassium 3-allyl-2,4-difluorophenyltrifluoroborate was prepared in a complex process consisting of lithiation - allylation of 2,4-difluorobromobenzene and conversion of the obtained product into a Grignard compound, formation of a BC bond in reaction with B(OEt)3 and finally hydrolysis in aqueous KHF2 solution. Potassium 3-phenylprop-2-enyltrifluoroborate, potassium 3-allyl-2,4-difluorophenyltrifluoroborate and 1-propargylpyrazole are characterized by spectroscopy (NMR) and melting points are determined for solid compounds. Conclusions: Potassium 3-phenylprop-2-enyltrifluoroborate and potassium 3-allyl-2,4-difluorophenyltrifluoroborate, were obtained as pure compounds, for which the process developed does not require the use of palladium catalysts for the 3-phenylprop-2-enyltrifluoroborate, which makes this method competitive with to found in the literature. The synthesis of potassium 3-(1H-pyrazol-1-yl)prop-1-enyltrifluoroborate requires further investigation of the hydroboration stage, it is necessary to check the reactivity of other hydroborating compounds. Synthesis of the intermediate - 1-propargylpyrazole should use potassium carbonate as a base and apply an excess of propargyl bromide. In general, further research is recommended to optimize the processes studied in order to obtain higher yields.
Diploma type
Engineer's / Bachelor of Science
Diploma type
Engineer's thesis
Author
Błażej Ogonowski (FC) Błażej Ogonowski,, Faculty of Chemistry (FC)
Title in Polish
Opracowanie procedury syntezy wybranych trifluoroorganoboratów
Supervisor
Tomasz Kliś (FC/CPC) Tomasz Kliś,, Chair of Physical Chemistry (FC/CPC)Faculty of Chemistry (FC)
Certifying unit
Faculty of Chemistry (FC)
Affiliation unit
Department Of Physical Chemistry (FC/CPC)
Study subject / specialization
, Technologia Chemiczna
Language
(pl) Polish
Status
Finished
Defense Date
05-02-2019
Issue date (year)
2019
Reviewers
Tomasz Kliś (FC/CPC) Tomasz Kliś,, Chair of Physical Chemistry (FC/CPC)Faculty of Chemistry (FC) Agnieszka Adamczyk-Woźniak (FC/CPC) Agnieszka Adamczyk-Woźniak,, Chair of Physical Chemistry (FC/CPC)Faculty of Chemistry (FC)
Keywords in Polish
trifluoroorganoboraty, kwasy boronowe, związki Grignarda, związki litoorganiczne
Keywords in English
trifluoroorganoborates, boronic acids, Grignard compounds, organolithium compounds
Abstract in Polish
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praca_inż_-Błażej_Ogonowski-_278406.pdf
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Identyfikator pracy APD: 29908

Uniform Resource Identifier
https://repo.pw.edu.pl/info/bachelor/WUT294406c820cc4bc99b41a21bfa6f70b3/
URN
urn:pw-repo:WUT294406c820cc4bc99b41a21bfa6f70b3

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