New Radical Reactions Enabled by In Situ Reaction Monitoring
In order to develop new synthetic methodologies or optimize desired reactions, it is ideal to have sound reaction insight (mechanistic and kinetic) to make conclusions and provide direction for future experiments. This presentation details how the Baxter Research Group incorporates fundamental principles of physical organic chemistry and chemically-specific trend data with high temporal resolution for kinetic analysis and reaction understanding. This presentation discusses how two experimental protocols for radical C-H fluorination reactions were developed. One protocol proves to be experimentally far superior to the other.
One example involves how observed IR trend behavior during reagent additions was unexpected and led to ideas to investigate the root cause of the reaction performance. Through additional experiments, computational evidence, and NMR spectroscopy, a revised mechanistic diagram via a reaction intermediate aided to explain the observed reaction behavior. Optimized reactions were now possible with the new reaction insight.
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This presentation covers:
- Aminoalkyl and substituted pyridine radical reactions for C-H fluorination
- Selectfluor as a weak oxidant and fluorine source
- In situ FTIR monitoring in an electrochemical cell
- Effect of reaction parameters (addition order, stoichiometry, substrate) tracked with inline FTIR
- New reaction chemistry from updated mechanistic insight
Who Should View This Presentation?
Process Chemists and Chemical Engineers working in the Pharmaceutical and Chemical Industries as well as in Academic Research.
Presenter: Ryan Baxter, Ph.D. - University of California - Merced
Professor Baxter earned his Bachelor of Science from the University of Wisconsin, Madison performing research in the laboratory of Professor Sam Gellman. He earned his Masters and Ph.D. from the University of Michigan while studying the kinetics of nickel-catalyzed reductive couplings with Professor John Montgomery. He then performed postdoctoral research with Professors Donna Blackmond and Phil Baran at the Scripps Research Institute. During this time, he was involved in the development of sulfinate radical precursors for heterocycle functionalization. He also investigated the mechanism of palladium-catalyzed olefinations in collaboration with Professor Jin-Quan Yu. During his independent career, Professor Baxter’s lab has developed new synthetic methods using radical chemistry from inexpensive or renewable radical precursors. His lab often relies on in situ reaction monitoring to streamline reaction development and discover new modes of reactivity.