Complexity-Generating Hydration Reactions via Metal-Catalysed Reaction of Boronic Acids with Alkenes

简单的有机分子含有碳-碳双键，被称为烯烃，是广泛使用的散装化学品，作为基本的起始材料，用于合成广泛的更复杂的分子与有用的性能-药物，精细化学品，农用化学品，聚合物等。在这个建议中，我们概述了新的催化策略，烯烃直接转化为复杂的分子结构。在每种情况下，通过在烯烃的碳-碳双键上正式加入一个水分子（水合反应）引发一系列新的反应。水与烯烃的反应可能难以完成，因为许多烯烃不溶于水。通常使用强酸（如硫酸）或汞盐（毒性很强）来实现。在这项研究中，我们将采用一种新的策略，该策略基于我们实验室以前的工作，其中水分子连接到有机含硼化合物上，使其能够“溶解”在有机溶剂中，并在合适的催化剂存在下更容易反应（在该项目中，基于钯等金属的更有效且毒性更小的催化剂，我们的初步实验已证明这些催化剂是有效的）。这种策略可能非常强大，因为硼原子可以用于进一步的（水合后）化学反应以构建复杂的产物。这些新的反应策略将用于合成广泛的产品，包括在医学研究中针对疾病靶点进行筛选的感兴趣的分子。这将使我们能够与适当的生物学家建立合作关系，以便将我们的新发现应用于新的医学治疗方法的开发。

Simple organic molecules containing carbon-carbon double bonds, known as alkenes, are widely available bulk chemicals that serve as basic starting materials for the synthesis of a wide range of more complex molecules with useful properties - pharmaceuticals, fine chemicals, agrochemicals, polymers, etc. In this proposal we outline new catalytic strategies for the direct conversion of alkenes into complex molecular structures. In each case, a novel sequence of reactions is initiated via the formal addition of a molecule of water across the carbon-carbon double bond of the alkene (a hydration reaction). The reaction of water with an alkene can be difficult to accomplish as many alkenes do not dissolve in water. It is usually achieved using either strong acids (e.g. sulfuric acid) or mercury salts (which are very toxic). In this research we will employ a new strategy based upon previous work from our laboratory in which the water molecule is attached to an organic boron-containing compound, enabling it to be 'dissolved' in an organic solvent and to react more readily in the presence of a suitable catalyst (In this project more efficient and considerably less toxic catalysts based around metals such as palladium, platinum and gold will be used - our preliminary experiments have demonstrated that such catalysts are effective). This strategy is potentially very powerful as the boron atom can be used in further (post-hydration) chemical reactions to construct complex products. These new reaction strategies will be of use for the synthesis of a wide range of products including molecules of interest for screening against disease targets in medical research. This will enable us to build up collaborations with appropriate biologists in order to apply our new discoveries in the development of new medical treatments.