High-throughput compatible catalyst development towards sustainable direct alkenylation reaction discovery and optimization

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dc.contributor.authorPipaon Fernandez, Nahiane
dc.contributor.supervisorLeitch, David
dc.date.accessioned2024-08-29T20:44:04Z
dc.date.available2024-08-29T20:44:04Z
dc.date.issued2024
dc.degree.departmentDepartment of Chemistry
dc.degree.levelDoctor of Philosophy PhD
dc.description.abstractThe direct C–H functionalization of heteroaromatic compounds such as pyridine, furan, thiophenes, thiazoles, and others have been developed as effective methods for making Csp2–Csp2 linkages which are often found in biologically active compounds and π-conjugated functional materials. More specifically, the development of palladium catalysts that can selectively activate specific C–H bonds is key for late-stage functionalization of pharmaceutically-relevant compounds. Mechanistic studies of the catalytic system, reaction intermediates and evaluation of the reaction parameters allows chemists maximize the reaction performance. This thesis explores direct C–H alkenylation reactions from both a catalyst and substrate perspective, and exploits modifications to the generally accepted direct alkenylation mechanism. Furthermore, this work shows how systematic, hypothesis-driven High-Throughput Experimentation of reaction conditions, palladium sources and ancillary ligands enables the development of new reactivity, optimization of catalytic systems and exploration of the chemical space of direct alkenylation of heterocycles. Finally, this work also highlights the versatility of palladacyclic precatalysts in the selective C–H functionalization of challenging but pharmaceutically relevant heterocycles such as pyrazoles and thiazoles. New synthetic procedures have been described toward the development of single component precatalyst systems, and they have been used for the synthesis of two pharmaceutical compounds: GSK3368715, a PRMT1 inhibitor, and fatostatin, a lipid accumulation inhibitor.
dc.description.embargo2025-08-19
dc.description.scholarlevelGraduate
dc.identifier.urihttps://hdl.handle.net/1828/20327
dc.languageEnglisheng
dc.language.isoen
dc.rightsAvailable to the World Wide Web
dc.subjectdirect alkenylation
dc.subjecthigh-throughput experimentation
dc.subjectreaction discovery
dc.subjectreaction optimization
dc.titleHigh-throughput compatible catalyst development towards sustainable direct alkenylation reaction discovery and optimization
dc.typeThesis

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