Professor Scott E. Denmark, the R. C. Fuson Professor of Chemistry at the University of Illinois, Urbana-Champaign, is the 2019 recipient of The Journal of Organic Chemistry Outstanding Publication of the Year Award Lectureship. He is being recognized for his research group’s article, “Catalytic Nucleophilic Allylation Driven by the Water-Gas Shift Reaction.”
Professor Denmark will receive a plaque, honorarium, and expenses paid to attend the 258th ACS Fall National Meeting & Exposition in San Diego, where he will receive his award and present the award lecture during a dedicated symposium. The session will also celebrate Gregory Beautner, recipient of the Organic Letters Outstanding Publication of the Year Award Lectureship for 2019.
This award honors the author of an outstanding letter published in JOC the previous calendar year that demonstrates creativity and impact in the field of organic chemistry and is sponsored by The Journal of Organic Chemistry and the ACS Division of Organic Chemistry.
“We are delighted to celebrate the contributions of Professor Denmark to JOC generally, and his team’s most recent, superb paper specifically. It is inspiring to see the synergy of creative concepts and depth of study together in this allylation chemistry made possible by the Water-Gas Shift Reaction,” says Scott J. Miller, Editor-in-Chief of The Journal of Organic Chemistry.
The Journal of Organic Chemistry Outstanding Publication of the Year Lectureship Session at the ACS Spring 2019 National Meeting & Exposition in San Diego
As the recipient of The Journal of Organic Chemistry Outstanding Publication of the Year Award Lectureship for 2019, Professor Denmark will present a lecture at an ACS Division of Organic Chemistry session in his honor at the 258th ACS Fall National Meeting & Exposition in San Diego. The session will also celebrate Dr. Gregory L. Beutner of Bristol-Myers Squibb, recipient of the Organic Letters Outstanding Publication of the Year Award Lectureship for 2019.
An Interview with Professor Scott E. Denmark
I connected with Professor Denmark recently to learn more about his research and his career in organic chemistry. These are the highlights of our conversation.
How did you become interested in this line of investigation?
The discovery of this reaction was a terrific example of serendipity. The project was sponsored by a company that wanted to carry out nucleophilic allylation of glucose on a huge scale, but their existing method used stoichiometric amounts of tin which created a great deal of toxic waste. Dr. Son Nguyen was attempting to follow a little known procedure that employed a tertiary amine as the reducing agent with a ruthenium catalyst. He was evaluating the reaction under an atmosphere of carbon monoxide in a steel bomb and found that no reaction took place after 24 h. However, after opening the bomb to check reaction progress and then closing it back up, he discovered that the reaction went to completion by the next check. He surmised that something was introduced during the opening of the bomb and we hypothesized that either oxygen or water from the atmosphere were the most likely candidates. After a bit of detective work, he discovered that water was the culprit and that we had stumbled upon the use of the water-gas shift reaction which provided the reducing potential needed.
How do you think this paper and your group’s research will progress further development in this area?
We have already demonstrated the application of the water-gas shift reaction for reductive alkylation and reductive formylation in subsequent publications. We are interested in pursuing reductive amination as well as other net reductive processes that currently employ sacrificial metals.
Tell me about your coauthors/research group and how you worked together to produce this piece.
Dr. Nguyen discovered the reaction, and the extension of the scope was first investigated by Dr. Selena Milicevic, both postdoctoral research associates. The first student to work on this reaction as a full-time graduate student was Zachery Matesich. Zack did the bulk of the work in the full article but wanted to include all of the previous investigations done by Son and Selena, so he compiled their results from very well written postdoctoral reports.
What’s next in your research?
This project is a small component of the overall research effort in the group. Check out my website for what is currently going on!
Is there anything else that you would like to share?
Some researchers are terrified of using carbon monoxide, but we have a very well designed apparatus and safety precautions. We have never had a leak or incident. I would like to thank the National Science Foundation for supporting our work.