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Sato, Yusuke

University of British Columbia

Real-time sample analysis, including in situ analysis and automated sampling/injection, provides timely measurements of analytes and facilitates efficient reaction elucidations. In contrast to manual sampling, real-time sample analysis eliminates laborious sample preparations and increases efficiency and robustness in obtaining data-rich information. Unfortunately, many instrumental analytical tools used for real-time reaction monitoring are only applicable to homogeneous conditions, leaving heterogeneous conditions a major challenge. This thesis explores developments and applications of new heterogenous sampling platforms to investigate reaction details. Combing commercially available laboratory equipment with an in-line dynamic mixer, an online HPLC reaction monitoring system has been developed to investigate solid/liquid heterogeneous reactions. Using this platform, a slurry tetrabenazine (TBZ) synthesis has been investigated. The isolation and characterization of unseen enone and iminium intermediates proved that the reaction underwent the aza-Michael-Mannich annulation pathway. Our increased mechanistic understanding has allowed for the reaction rate to be boosted five-fold. For liquid/liquid heterogeneous reaction monitoring, a phase-selective sampling system was developed. This was achieved by developing a novel hydrophilic/oleophobic stainless steel filter. Partition coefficients of boronic acids with varying functional groups have been tested using this platform. Biphasic Suzuki-Miyaura coupling reaction was also explored. In addition to the heterogeneous conditions, nanocluster synthesis was also known to create challenging conditions to be monitored due to its complicated polydisperse cluster formations. This thesis lastly demonstrated that real-time LCMS monitoring revealed size growth of gold nanoclusters synthesis and potential intermediates.

Text

2023-01-13

Attribution-NonCommercial-NoDerivatives 4.0 International

http://hdl.handle.net/2429/83641

Chemistry

University of British Columbia

UBCV

http://creativecommons.org/licenses/by-nc-nd/4.0/