CasCat: Cascade Catalysis for Late-Stage C-H Functionalization

Moderne medisin og teknologiske innovasjoner avhenger av designede molekyler med spesialiserte egenskaper. For å kunne lage disse viktige molekylene trenger man en rekke kjemiske metoder som har blitt utviklet de siste tiårene. I dette prosjektet ønsket vi å utvikle nye, praktiske og mer miljøvennlige kjemiske metoder som vil muliggjøre produksjon av nødvendige nye molekyler for både medisin, miljøforskning og organisk materialforskning. Våre nye kjemiske metoder vil gi molekylene de unike egenskapene som gjør dem godt tilpasset anvendelsene. Noen av de nye metodene anvender synlig lys eller andre "grønne" energikilder og kan derfor bli mer miljøvennlige teknologier. Prosjektet har ført til nye metoder og molekyler som er relevante for blant annet medisinalutvikling, overflatebehandling, PET-diagnostikk og måling av metangass i miljøovervåkning, og derfor forventer vi samfunnsmessige konsekvenser av dette grunnforskningsprosjektet i fremtiden.

CasCat has generated several new and improved green and efficient chemical methods which will be impactful. Two chemical companies have contacted the principal investigator to enquire about methods that we have published, thus demonstrating interest and potential impact of these methods. CasCat has further produced a large amount of knowledge of de novo heterocycle synthesis and chemical functionalization processes, and the challenges involved, and thus greatly enhanced the competencies of the project participants. The project results have generated novel branches of research directions and enabled highly efficient procedures for generating some heterocycles. The project has enabled the synthesis of novel molecules with a range of potential applications, such as in medical imaging, drug design, antifouling agents, environmental sensor technology and veterinary medicine. Notably, synthetic natural product analogues generated in the project have displayed antifouling activity as well as inhibitory effects on human AChE receptors, thus suggesting potential medical and surface materials applications. The wide variety of potential applications of the project results have led to a large range of international and transdisciplinary research collaborations and thus, knowledge transfer between disciplines and nations in chemistry and applied areas.

In this proposal, we aim to develop novel late-stage C-H functionalization approaches to modify compounds of immediate relevance to medical and sensor technologies. Our Late-stage functionalization approach will enable a more effective molecular development process by greatly reducing the number of structural skeletons that have to be made. Moreover, environmental and economic strains associated with chemical synthesis will be reduced. The project entails developing catalysts and methods based on visible-light propelled catalysis in conjunction with palladium and copper catalyzed coupling technology, which enables predictable yet novel architectural modifications of complex molecular systems. Molecules with immediate applications in medical imaging and gas sensors will be produced using the novel approach as proofs of concept and applicability. The experimental work will be conducted by one postdoctoral researcher and one doctoral candidate, under the supervision of an early-career researcher, over a period of 4 years, in collaboration with national and international experts in intersecting research fields and chemical education. The project will greatly impact molecular design for materials and medicine by making structural modifications considerably more effective and producing a range of novel compounds for applications.