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01.07.2008



Interview: The chemistry [r]evolution



30 June 2008



Mike Doyle talks to Emma Shiells about evolution in chemistry, from Doyle's catalyst to how water saved the day









Mike Doyle Mike Doyle is Professor and Chair of the Department of Chemistry and Biochemistry at the University of Maryland, Baltimore, US. His research is focused on applications with metal carbene transformations, Lewis acid catalysed reactions, and selective catalytic oxidations. He is the new associate editor for organic chemistry in Chemical Communications.

 


What inspired you to become a scientist?


I came into science at a time when the Sputnik revolution was occurring in the US. I had a high school teacher who was very inspirational. He was a very short fellow, but when he talked about chemistry, he levitated! It was this teacher that taught me that chemistry was the place to go.


Why did you choose to study transition metal catalysis in organic synthesis?


I started my career looking at processes surrounding dinitrogen compounds, or nitrogen in general. Looking at the aspects of catalysis became a natural progression. We looked at catalysis in biological systems, then at rhodium-catalysed systems because they had just emerged on the scene. The work was a success; it evolved faster than all of the other areas we were working on.


Were any of your projects taken on commercially?


In the 1990s, we developed a set of rhodium catalysts - carboxamidates - that had chiral ligands; those systems became known as the Doyle catalysts. They were commercialised and have been used in industry and universities.


What achievement are you most proud of in your career to date?


Developing the Doyle catalysts was one achievement, but there was also the study on the role of nitrite in medicine in the 1980s. We had elaborated the mechanism of how nitrite acts as a nitric oxide donor in biological systems, in studies with haemoglobin and myoglobin. Unfortunately, in the mid 1980s, we had to drop this research due to lack of funding. Then, in the late 1990s, this became a very popular area and in early 2000, conferences were being held on the biological and physiological effects of nitrite. I attended a meeting in 2005, at the National Institutes of Health, talking about nitrite in medicine and physiology and I was introduced as the 'father' of the area. I took a lot of pride in that.


Is your research more biological now?



"Whatever you are doing should evolve. It's not a revolution anymore - it's an evolution"

No, it is more catalytic now. You can't stay in a particular area for too long these days, because of the nature of how chemistry evolves. Whatever you are doing should evolve. It's not a revolution anymore - it's an evolution. We have evolved catalysis, starting from our initial work using catalysts for metal carbene formation, to Lewis acid catalysed reactions, to oxidation chemistry and, more recently, to materials.


Where do you get your ideas from? What inspires you?


Stress is one thing! Or knowing that you have to make changes. When something confounds you, but you can't understand how it happened or why it happened, that leads to change. Students also drive you. A very good student will say 'I'm not going to do the same thing as the person in front of me; I want to do something different.' And they head off in directions that you would never have taken yourself.


What other projects are you working on at the moment?


One project is the use of chiral catalysts in asymmetric transformations, in particular metal carbene related transformations, especially ylide transformations, which are underutilised in chemistry today. The other is Lewis acid promoted reactions - we are trying to offer new and highly effective catalysts for that. We are also bringing catalyst loading down to commercial levels. The third is oxidation chemistry and, more recently, materials chemistry related to the metals we have been using in catalysis.


What is your ultimate goal?


I think broadening the catalysts' applications, and understanding the features that make them unique among catalysts. If I could do that in my lifetime, I would be happy.


You are the new associate editor for Chemical Communications. What do you hope to achieve in your new role?


To increase the visibility of Chemical Communications in the organic chemistry community, by showing the advantages of Chemical Communications, and by highlighting the fact that it would be a very good component of an overall research publication portfolio. 


Can you remember any tense moments in the lab? 



"I remember saying 'we got it wrong for the abstract, we got it wrong for the disclosure, my career is over!' All I had to do was add water. It was that simple!"

Very early in my career, as a young assistant professor, I conducted preliminary experiments that involved the reduction of carbonyl compounds with organosilanes. Our group had submitted an abstract for a national meeting describing the methodology and, at the same time, had submitted a disclosure for a patent application. About a month after we had submitted the abstract, we realised that the method was wrong. It happened on the 4th of July. I was in the lab, carrying out the reaction. I made the correct mixture, as we had done before, and I had that moment where everything becomes clear and I realised I had got it wrong. I remember saying 'we got it wrong for the abstract, we got it wrong for the disclosure, my career is over!' Then, a few minutes later, I had the solution. All I had to do was add water. It was that simple!


If you could go back into a lab at any time in history, what experiment would you love to do?


If I was back in the 1970s, I would have looked into asymmetric catalysis. It has taken me many years to be as deep into catalysis as I am now. I would take a Lewis acid catalyst and build chiral surroundings for it - metal or organic - and apply it to a common reaction to see what I'd get. At that time [in the 1970s], catalysis consisted of only two processes - hydrogenation and metal carbene chemistry. 


Which scientific discovery would you have liked to have been responsible for?


Developing the first catalytic concept, which happened in the 1960s. The first reaction to use a chiral catalyst, or a catalyst with a ligand, to induce chirality in something that is not chiral, was almost like playing God. I have always found that to be one of the really great scientific achievements. 


If you weren't a scientist, what would you be?


When I was in college, I decided not to be a physician of any sort because I couldn't handle the sight of blood. I recall an instructor saying 'you might study law' and that was something that I had considered at one time. However, I think science has always attracted me, and perhaps, if I had the choice again, I might have gone into biochemistry and the biosciences. 










Related Links







Link icon Mike Doyle's homepage
at the University of Maryland






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Related Links



Synthesis of bis(-aryl)dirhodium(III) caprolactamates by oxidative arylation with arylboronic acids
Jian-Hua Xie, Jason M. Nichols, Conrad Lubek and Michael P. Doyle, Chem. Commun., 2008, 2671
DOI: 10.1039/b806283h



Oxidation of secondary amines catalyzed by dirhodium caprolactamate
Hojae Choi and Michael P. Doyle, Chem. Commun., 2007, 745
DOI: 10.1039/b615805f


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