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Study and Development of Boron-mediated Amidation Reactions

Karaluka, Valerija; (2017) Study and Development of Boron-mediated Amidation Reactions. Doctoral thesis , UCL (University College London).

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Abstract

This thesis discusses the study and further developments of boron-mediated amidation reactions. Chapter I introduces the conventional and recent methods and developments for the direct amidation of carboxylic acids and their derivatives. An overview of boron-mediated transformations is also given with the focus on stoichiometric methods and boronic acid catalysts. Chapter II describes the utilisation of B(OCH2CF3)3 in the synthesis of medicinally-relevant amides, selective monoacylation of symmetrical diamines, and amidation of unprotected amino acids. Design of Experiments (DoE) is applied as the optimisation method for the improvement of efficiency of the amidation reaction and therefore the yield of one of the medicinally relevant amides. Furthermore, a convenient derivatisation method of amino amide products is applied to determine enantiopurity of the products. Chapter III discusses investigations performed with the aim of understanding boron-mediated amidation reactions. A spectroscopic study is provided along with the proposed tentative mechanism. Chapter IV describes the design and synthesis of a potential boronic acid amidation catalyst, which incorporates a borate moiety. Conclusions and future developments as well as an outlook of the applications of borates in organic synthesis are described in Chapter V. Chapter VI provides experimental details of this work and full characterisation of compounds synthesised throughout this project. Chapter VII contains an appendix that includes chiral HPLC and spectroscopic data from Marfey’s reagent derivatisation of chiral amino acid amide products. Moreover, spectra from 11B NMR study of boron-mediated amidations and the DoE study for the optimisation of decarboxylation of amino acids are included.

Type: Thesis (Doctoral)
Title: Study and Development of Boron-mediated Amidation Reactions
Event: UCL
Language: English
UCL classification: UCL > Provost and Vice Provost Offices
UCL > Provost and Vice Provost Offices > VP Research
URI: http://discovery.ucl.ac.uk/id/eprint/1571141
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