RSC Advances HOT articles – a feature interview with Frédéric-Georges Fontaine

We are very pleased to introduce Frédéric-Georges Fontaine, corresponding author of the paper ‘Boric acid as a precatalyst for BH3-catalyzed hydroboration‘. His article has been very well received and handpicked by our reviewers and handling editors as one of our HOT articles. Frédéric-Georges told us more about the work that went into this article and what he hopes to achieve in the future. You can find out more about the author and his article below and find more HOT articles in our online collection.

Meet the author

Frédéric-Georges Fontaine got his B.Sc. in Chemistry from Université de Montréal in 1998 and a Ph.D. in Organometallic Chemistry from the same institution in 2002 under the supervision of Davit Zargarian. After a NSERC postdoctoral fellowship at UC Berkeley with T. Don Tilley, he started at Université Laval (Quebec City, Canada) in 2004, where he is a Full Professor since 2013. His research is focused on the development of metal-free catalysts for the C-H functionalization and CO2 reduction. He is a Japanese Society for the Promotion of Science alumni and holds a Canada Research Chair in Green Catalysis and Metal-Free Processes since 2018. He is the director of the NSERC CREATE Center for Innovation and Research on Carbon Utilization in Industrial Technologies (CIRCUIT) since 2020.

The research group

The co-authors; Hoang-Minh To and Julien Légaré Lavergne

Could you briefly explain the focus of your article to the non-specialist (in one or two sentences only) and why it is of current interest?
We demonstrate in this article that air-stable boric acid can convert into reactive BH3 under catalytic conditions. This study is of interest because it provides a safer way to do BH3 type transformations, like the hydroboration of esters as reported herein.

How big an impact could your results potentially have?
This discovery could affect the way BH3-catalyzed reactions are carried out. In the last decade, boranes have been playing an important role as metal-free catalysts for important transformations like C-H bond functionalization and hydroboration catalysis, and this chemistry could provide insights on developing greener and safer catalytic systems.

Could you explain the motivation behind this study?
Initially, we wanted to explore the reactivity of Frustrated Lewis pair aminoborane catalysts for the reduction of esters. By doing our control experiments, we discovered that BH3 is the active catalyst. In our attempt to simplify the catalytic system, we found out that boric acid could do this transformation as well as BH3.

In your opinion, what are the key design considerations for your study?
We are looking for green precatalysts that are air-stable, cheap, safe and easy to handle. Boric acid fills all these parameters.

Which part of the work towards this paper proved to be most challenging?
Monitoring the conversion of the esters over time while using microwave irradiation as the energy source was challenging. It required performing an experiment for each single condition and reaction time, which was quite time consuming. However, the results are worth the efforts.

What aspect of your work are you most excited about at the moment?
The consumption of boric acid in the presence of pinacolborane made us realized that the functional groups on boron undergo rapid exchange. This kind of process, called transborylation in recent reports, has the potential to widen the extend of boron chemistry.

What is the next step? What work is planned?
Using pinacolborane to convert boric acid into BH3 is interesting, but this process could be much more compelling if a milder and cheaper hydride source was used instead of pinacolborane. We intend to try find more convenient hydride sources.

 

Boric acid as a precatalyst for BH3-catalyzed hydroboration
Julien Légaré Lavergne, Hoang-Minh To and Frédéric-Georges Fontaine
RSC Adv., 2021,11, 31941-31949

DOI: 10.1039/D1RA05945A, Paper

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