Commendation for Dr Alastair Lennox - School of Chemistry

Supervisor: Professor Guy Lloyd-Jones

Funding: EPSRC Industrial CASE Award with AstraZeneca

     

PhD Project: Organotrifluoroborate preparation, coupling and hydrolysis

Alastair’s thesis concerned the mechanism the “Suzuki-Miyaura coupling” of organoboronic acids, a reaction widely used in the synthesis of pharmaceuticals, agrochemicals, LCDs and organic LEDs, and subject of the Nobel Prize in Chemistry (Suzuki, 2010). Recently, organotrifluoroborates have been widely adopted as advantageous replacements for the boronic acid, and Alastair set out to identify their mode of action. Carefully designed heteronuclear NMR, kinetic, and isotopic labelling experiments, and an ability to 'think outside the box', identified a range of processes that slowly release the boronic acid and thereby reduce the major side reactions. As part of this work, Alastair also designed a new, safe and scalable, route for preparation of the organotrifluoroborate reagents, avoiding the extensive etching of reactor vessels that the current route entails; this procedure is already being applied industrially.

Alastair’s work was published in four papers in the premier journals in the field, attracting extensive international attention and being highlighted in C&E News and Chemistry World. All four papers elicited exceptional peer review commentary, for example "This contribution is bound to be a classic, filled with remarkable details and analysis that explains much that defied prior explanation."

Alastair presented his research at national and international conferences, received 3 ‘best lecture’ prizes, 5 ‘best poster’ prizes (including first prize at the national Pfizer Organic poster competition), and was one of the 45 candidates shortlisted worldwide for the highly competitive Reaxys PhD thesis prize (2012).

Biography

I grew up in Nether Poppleton, a village outside York, and attended Bootham School in the city centre. After A-levels I spent a year back-packing and volunteering in Africa. On my return, attracted by the vibrant music scene and big-city life, I decided to move to Manchester to study chemistry. From there it took three years of hard work, including one at UCLA, and a multitude of painfully confusing courses before the penny began to drop and my love for the subject began to flourish. In my fourth and final year, my masters project with Dr Ian Watt, an inspirational mentor, led me to the idea of a PhD.

Being interested in mechanistic chemistry naturally led me to Professor Lloyd-Jones, who is one of the leading figures in the world. Luckily for me, he was at Bristol, which I found to be perfect at providing whatever I wanted out of a city. I was immediately impressed by the standard of research in the School of Chemistry. Being surrounded by so many knowledgeable, successful and intelligent people was initially daunting, but it soon grew to be inspirational and supportive. The School’s facilities and aspirations are world class, and I will look back at my time in Bristol as a very happy and productive period. My ultimate career goals are undecided, but I am currently co-writing a book on mechanistic chemistry, and following this, will broaden my scientific horizons as a post-doc abroad.