Synthesis and Suzuki-Miyaura Cross-Coupling of α-Borylated Pyrrolidines

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.