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Cracking a 20-year puzzle -- unravelling the mechanism of organo-copper catalysts

SimonWoodward445x124

Groundbreaking research led by Simon Woodward,a professor of synthetic organic chemistry at the University of Nottingham, has proved how a catalyst (a small atomic-sized ‘machine’ that knits together new molecules) in organo-copper chemistry works.

This is one of the key approaches of modern chemistry to making larger molecules.  

Scientific mystery

The reaction, known as asymmetric conjugate addition, has been a mystery to scientists who have been trying to understand the mechanism by which certain aluminium-containing chemicals ‘join together’ for 20 years. Prof Woodward and his team carried out hundreds of experiments over five years, in a bid to understand how these molecular machines work. They concluded that the reaction is effectively like a game of badminton, where the shuttlecocks are the reacting molecules. The research has been published in ACS Catalysis, and highlighted by the American Chemical Society as one of its top papers published globally this year.  

Speaking about the findings, Professor Woodward said, “I am delighted with the success of our research because it took us more than four years to work out the science carefully enough to get the key results. It is a very satisfying outcome to be able to derive understanding of what small unseen molecules are doing: like doing a cryptic crossword and completing it in double quick time. It’s particularly challenging in this case as it’s a crossword people have being trying to do for 20 years without success.”

The compounds involved in the Nottingham study catch fire in air and decompose at room temperature. Technically extremely difficult experiments at low temperature were needed to understand how the catalyst works. Professor Woodward’s team believe that the fundamental understanding they have attained will allow the development of future catalysts of higher efficiency.  

Broad range of applications

The research has a broad range of applications from medicinal studies to making materials for better technology. Possible examples include: Synthesis of analogues of cell wall components for anti TB studies, preparation of biologically active alkaloids, and sustainable and green routes to rare scents/perfumes. In all of these cases only one of two potential mirror image related compounds that can be prepared is useful pharmaceutically so designing catalysts that can do this effectively depends significantly on understanding how they work.

Professor Woodward’s research was carried out in the University’s new state-of-the-art GlaxoSmithKline Carbon Neutral Laboratory (CNL), which is a Centre of Excellence for sustainable chemistry focusing on research that is of particular relevance to the pharmaceutical industry.

 You can see the experiment in action on the Woodward Group website.

http://www.nottingham.ac.uk/~pczsw/SWGroup/

Posted on Tuesday 26th September 2017

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