Our group coined the term "CADA". The first discovery of the general mode of this reaction was an amazing and exciting moment for us in our research. It’s not just a single reaction, it can be utilised across a whole range of different transformations and this has since received a lot of interest. This was a really exciting moment for us!
What has been the most challenging moment of your career so far?
For me, the starting point of my independent career was challenging. You need to build a team, and learn how to manage your group, as well as develop any initial ideas that you have for your research. At the start, you do have plans, but you don’t know how they will turn out, so you have to be sure that you are pushing your team in the right direction.
What is your favourite reaction and why?
I thought I would say a dearomatisation reaction, but actually the first reaction that came to my mind was asymmetric C-H bond activation for the preparation of planar chiral ferrocenes. The reason for this is that during my PhD, I was involved in preparing planar chiral ferrocene compounds for use in palladium catalysis. The synthetic route that I used at that time was incredibly tedious and time consuming, because you were required to introduce central chirality during the disatereoselective synthesis, and then remove the central chirality.
Through the development of a C-H bond activation reaction for ferrocenes, we were instead able to use a readily available starting material, and the target planar chiral ferrocene could be obtained much more easily. This reaction is therefore a favourite of mine as it was a direct example of a process being much improved.
Where do you look to for inspiration?
Our groups meetings are great for this, as we are able to talk about problems in organic synthesis and how to overcome these. Also, before I took the position at the Shanghai Institute of Organic Chemistry, I worked in the pharmaceutical industry for two years. The demand for optimised applications for this industry are a big inspiration for me. The chemical space is much less explored in medicinal chemistry, so I’m always curious to explore this area to try to make useful drug-like chemical scaffolds.
When having your papers peer-reviewed, what has been the most helpful or interesting comment that you have received from reviewers?
Peer review can be incredibly helpful in providing a different angle through which to look at your research. I remember a specific example for one of our 2016 publications in the Journal of American Chemical Society that discussed C-H bond activation through the coupling of ferrocene to another aromatic compound. We included an indole substrate in this transformation, and we always believed that the indole substrate would react at the C3 position as this made sense logistically. The reviewer challenged us, asking what evidence we had for this taking place at the C3 position. When we really thought about this comment and carried out further characterisation, including crystal structure characterisation, we found out that it actually reacted at the C2 position! This is one case that I remember very clearly.
Sometimes reviewer comments can also really help you to delve further into mechanistic details. It can be difficult when a reviewer asks for more insight into the mechanism behind a certain reaction as you can spend weeks or even months looking into this without a definitive conclusion. However, in some cases this has actually led to us discover side reactions that we didn’t know were taking place, and can sometimes help you to discover new reactions all together! This can therefore be really helpful.
You have published over 10 papers with Chemical Science since your first publication with us in 2011. Of these papers, which one do you feel has made the most significant contribution to your area of research and why?
I love all my papers in the journal, but there is one particular paper from 2014 where we used iridium catalysis to initiate an intermolecular asymmetric allylic dearomatisation reaction of indoles. This paper really showcased the advantage of CADA reactions – the starting materials are readily available, you can use simple indoles, the catalyst used is relatively easy to get, the conditions are mild, and products are very useful. From this, we were able to demonstrate the asymmetric total synthesis of natural product (−)-debromoflustramine B in only 3 steps. This is an even better standard than what we can achieve today, so this paper really highlighted the utility of this method with a simple and efficient protocol.
You were involved in initial discussions prior to Chemical Science being launched back in 2010. Can you tell us about your involvement in these discussions?
I’d known Rob Eagling [previous Executive Editor for Chemical Science] for a long time and I was involved in talks about the journal quite early on. One thing we talked a lot about was the concept and idea of the Edge article, and even today I think this is really such a nice feature for Chemical Science. When you look at other journals, they are still struggling with restrictions around manuscript types, word limits etc. This is really annoying for authors. I do think the best way is the way that Chemical Science are doing things – the Edge article. Authors can take the space required to tell their story – if the story is long then it is long; if the story is short then it is short. I really like this feature.
When this was initially discussed, I really thought it would be a pipe dream, but it’s great that Chemical Science managed to push this idea forward. It really is great.
The year is 2030. How do you feel your area of research will have advanced by this time?
I would like to gain a better understanding of the chemistry that we’re doing. We’re always pushing for new advances, but I think in these coming years we will know more general rules for C-H bond activation or dearomatisation reactions. I’d also like to see our reactions really benefit a number of different applications, especially in the pharmaceutical industry.
We need to work hard!
10th anniversary collection
To celebrate the 10th anniversary of Chemical Science we are publishing a number of special birthday issues, to recognise and thank members of our community who have been supporting the journal and publishing in Chemical Science since we launched ten years ago.
Explore our collection now.