UBC Theses and Dissertations

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UBC Theses and Dissertations

Leveraging boron and fluorine : synthesis of organoboronates for radiolabeling and suzuki coupling of acylboronate MIDA esters Lai, Samson Hau Feng


This thesis presents a new synthesis of acylboronate esters from vinylboronates. These acylboronate esters are synthesized from vinylboronate MIDA (N-methyliminodiacetyl) esters that are either bought or hydroborylated from alkynyl-derivatives. In Chapter 2, a two-step oxidative process involving Upjohn dihydroxylation and Lemieux-Johnson conditions to make the desired acylboronate MIDA ester is disclosed. This includes the work by myself including the synthesis of some key substrates that would be used for the synthesis of bi-modal sensors for acyl trifluoroborates. Chapter 3 describes the application of the previously synthesized acylboronate MIDA esters for Suzuki-Miyaura cross coupling (SMCC). There are no prior studies on the cross-coupling of this organoboron species, therefore, I designed and optimized a scheme for the cross-coupling between phenacylboronate MIDA ester and aryl bromides. I successfully synthesized benzophenone derivatives from the previously mentioned materials at moderate yields. Further research is done on non-aroyl starting material derivatives, but did not yield cross-coupling and possibly led to ß-hydride elimination or rapid acylboronate decomposition.

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