A new coupling protocol for the synthesis of carbon-rich compounds.

Lead Research Organisation: Durham University
Department Name: Chemistry


The preparation of organic compounds, including advanced organic materials, depends heavily on the ability to generate bonds between carbon centres selectively, and preferably under mild (e.g. relatively low temperature) conditions. Mild conditions are especially important in the preparation of compounds which feature a high degree of unsaturatation and are often highly reactive unless protected by large stabilising groups. To this end many people have been working a wide range of C-C bond forming reactions catalysed by a number of different metals, but often which feature a combination of palladium and copper.Professor Bruce at the University of Adelaide has discovered a new reaction that allows the formation of C-C bonds from gold reagents. At first this might seem something of a backwards step, given the perceived expense of gold. However, there are some particular advantages to the gold chemistry. For example, the reactions proceed at room temperature in ether or thf rather than the usual (and potentially more reactive) amine solvents used in the established copper and palladium-catalysed chemistry. In addition, the gold is recovered after the reaction, in a chemical form that can be collected and re-used directly. We now hope to be able to take the reaction on one step further and use this gold chemistry to effect multiple sequential C-C bond forming reactions in the same molecule before separating it from the desired product and recycling. Gold reagents are also particularly easy to prepare and can handled in air. This is a great advantage when dealing with acetylenic compounds, as the corresponding copper compounds are prone to explosive decomposition. We propose to use the new Bruce C-C coupling reaction together with easily prepared and handled gold derivatives of acetylenes to prepare a range of highly unsaturated carbon compounds. These compounds may one day find use as advanced materials, but at this stage we would really seek to develop the chemistry to a stage where it can be used by others.To make this happen, we would like to bring Professor Bruce to the UK where he can work with Dr Low's group and help develop this chemistry. This project therefore seeks to use the particular combination of experience offered by Professor Bruce in his coupling chemistry and Dr Low, who has developed a range of experience with high-carbon content materials through not only his PhD studies with Professor Bruce, but also through his postdoctoral work in Canada with Arthur Carty and his own work with cross-conjugated carbon frameworks in Durham. We would also like to broaden the number of people who can benefit from Professor Bruce's time in the UK, and to do this we propose that Professor Bruce give a series of lectures and seminars not only in Durham, but also at other university chemistry departments around the country.


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Man W (2011) Cross-coupling reactions of gold(I) alkynyl and polyyndiyl complexes in Journal of Organometallic Chemistry

Description Leadership Fellowship
Amount £1,103,718 (GBP)
Funding ID EP/H005595/1 
Organisation Engineering and Physical Sciences Research Council (EPSRC) 
Sector Public
Country United Kingdom
Start 10/2009 
End 06/2013