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Theme 2 colloquium: "“Remote Activation Strategies for O-Glycosylation and C-H Functionalization” (Lecture)

Tuesday 9 April 2019Add to my calendar
from 16:00
prof. Justin Ragain (Louisiana State University, USA)

Justin R. RagainsThioglycosides and C-H bonds are known by practitioners of organic synthesis for the difficulties incurred in their activation. However, these "functionalities" may hold little else in common. Nevertheless, we have found that remote activation strategies are an excellent approach for the activation of both. With our approaches, relatively easily generated, high-energy intermediates undergo intramolecular reactions that result in the activation of remote thioglycosides and C-H bonds. In the case of thioglycosides, we have demonstrated that visible-light activation and acid catalysis result in glycosyl sulfonium ions that further react with alcohols to generate O-glycosides. In the case of C-H bonds, we have shown that generation of aryl radicals using redox-active catalysts results in hydrogen-atom-transfer processes from remote C-H bonds leading to alkyl radicals that undergo further reaction. The scope of these reactions and mechanistic details will be discussed.

Drinks afterwards on Huygens 3rd floor!

dr. Evan Spruijt & dr. Peter Korevaar