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

用于合成富碳化合物的新偶联方案。

基本信息

批准号：
EP/D053668/1
负责人：
Paul Low
金额：
$ 4.35万
依托单位：
Durham University
依托单位国家：
英国
项目类别：
Research Grant
财政年份：
2006
资助国家：
英国
起止时间：
2006 至无数据
项目状态：
已结题

来源：
https://gtr.ukri.org/projects?ref=EP%2FD053668%2F1
关键词：
new coupling protocol synthesis carbon

项目摘要

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.

有机化合物的制备，包括先进的有机材料，在很大程度上取决于选择性地在碳中心之间产生键的能力，并且最好是在温和（例如相对较低的温度）的条件下。在制备具有高度不饱和的化合物时，温和的条件尤其重要，除非有大的稳定基团保护，否则通常具有高活性。为此，许多人一直在研究由许多不同金属催化的各种C-C键形成反应，但通常以钯和铜的组合为特征。阿德莱德大学的布鲁斯教授发现了一种新的反应，可以让金试剂形成C-C键。乍一看，考虑到黄金的价格，这似乎是一种倒退。然而，金化学有一些特殊的优点。例如，反应在室温下在乙醚或乙醚中进行，而不是在已建立的铜和钯催化化学中使用的通常（并且可能更活跃的）胺溶剂。此外，在反应之后，金以一种可以直接收集和再利用的化学形式被回收。我们现在希望能够将反应推进一步，并在将其与所需产物分离并回收之前，利用这种金化学在同一分子中影响多个顺序的C-C键形成反应。金试剂也特别容易制备，可以在空气中处理。当处理乙炔化合物时，这是一个很大的优势，因为相应的铜化合物容易爆炸分解。我们建议使用新的Bruce C-C偶联反应与易于制备和处理的乙炔金衍生物一起制备一系列高不饱和碳化合物。这些化合物可能有一天会被用作高级材料，但在这个阶段，我们真的会寻求将化学发展到可以被其他人使用的阶段。为了实现这一目标，我们想把Bruce教授带到英国，在那里他可以和Low博士的团队一起工作，帮助开发这种化学物质。因此，该项目寻求利用布鲁斯教授在耦合化学方面的经验和Low博士的特殊结合，Low博士不仅通过布鲁斯教授的博士研究，还通过他在加拿大与亚瑟·卡蒂的博士后工作以及他自己在达勒姆的交叉共轭碳框架的工作，在高碳含量材料方面积累了一系列经验。我们也想让更多的人受益于布鲁斯教授在英国的时间，为了做到这一点，我们建议布鲁斯教授不仅在达勒姆大学，而且在全国其他大学的化学系举办一系列讲座和研讨会。