Howman, Chloe Elizabeth ORCID: 0000-0003-0910-2348 (2021) Synthesis and Suzuki-Miyaura Cross-Coupling of α-Borylated Pyrrolidines. MSc by research thesis, University of York.
Abstract
This thesis describes the steps taken towards the development of a methodology for the synthesis and Suzuki-Miyaura cross-coupling of α-borylated pyrrolidines. Two main methods were explored for the synthesis of α-borylated pyrrolidines. A Rh-catalysed approach, reported in Section 2.2, was unsuccessful in our hands. In contrast, the use of lithiation-trapping chemistry described in Section 2.3 delivered gram quantities of 2-B(pin) N-Boc pyrrolidine A without the need for chromatography. Using this method and subsequent N-functionalisation or boronate modification, a range of other α-borylated pyrrolidines (B-G) were prepared for subsequent Suzuki-Miyaura cross-coupling studies. Two sets of conditions, described in Section 3.2, were investigated for the Suzuki-Miyaura cross-coupling to form α-arylated pyrrolidines, one focusing on B(pin) functionalised pyrrolidines and the other applied to BF3K functionalised pyrrolidines, but unfortunately, these reactions were not successful.
Metadata
Supervisors: | O'Brien, Peter |
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Keywords: | Pyrrolidines, heterocycles, Suzuki-Miyaura, cross-coupling, borylation, methodology, lithiation, Bpin, Rh-catalysis, N-functionalisation, arylation |
Awarding institution: | University of York |
Academic Units: | The University of York > Chemistry (York) |
Depositing User: | Miss Chloe Elizabeth Howman |
Date Deposited: | 11 Nov 2021 12:09 |
Last Modified: | 11 Nov 2021 12:09 |
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