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Synthesis of amides using boron catalysts

Sabatini, Marco; (2018) Synthesis of amides using boron catalysts. Doctoral thesis (Ph.D), UCL (University College London). Green open access

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Abstract

The thesis describes the research conducted towards the development of more sustainable methods for amide bond formation. The first chapter describes the importance of amide bond formation and the methods currently used for this type of transformation. Crucially, current methodologies defy in many aspects the 12 principles of green chemistry and are thus not sustainable. The subsequent chapters describe the work conducted directed at addressing problems with the current state of the art of amide bond formation. The development of a novel catalytic method for direct amidation of carboxylic acids with amines using borate esters is described. The applicability of this method for the synthesis a wide selection of amides and pharmaceutically relevant compounds is discussed and the extension of this methodology with unprotected amino demonstrated. Studies were also conducted towards understanding the mechanism of boron catalysed systems for amidation. A mechanistic hypothesis for borate systems based on kinetic studies, NMR studies and isolated reaction intermediates was elaborated. Conclusions and future outlooks based on these findings are presented.

Type: Thesis (Doctoral)
Qualification: Ph.D
Title: Synthesis of amides using boron catalysts
Event: UCL
Open access status: An open access version is available from UCL Discovery
Language: English
UCL classification: UCL
UCL > Provost and Vice Provost Offices
UCL > Provost and Vice Provost Offices > UCL BEAMS
UCL > Provost and Vice Provost Offices > UCL BEAMS > Faculty of Maths and Physical Sciences
URI: https://discovery.ucl.ac.uk/id/eprint/10045230
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