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

通过硼酸与烯烃的金属催化反应产生复杂的水合反应

基本信息

批准号：
EP/J01432X/1
负责人：
Tom Sheppard
金额：
$ 43.98万
依托单位：
University College London
依托单位国家：
英国
项目类别：
Research Grant
财政年份：
2012
资助国家：
英国
起止时间：
2012 至无数据
项目状态：
已结题

来源：
https://gtr.ukri.org/projects?ref=EP%2FJ01432X%2F1
关键词：
Complexity Generating Hydration Reactions via

项目摘要

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.

简单的有机分子含有碳碳双键，称为烷烃，是广泛可用的大量化学物质，可以用作合成具有有用特性的广泛的更复杂的分子的基本起始材料，这些特性（药物，精细的化学品，高化学物质，硬化学物质，聚合物等。在每种情况下，通过在烯烃的碳碳双键（水合反应）中形式添加水分子来启动新的反应序列。由于许多烷烃不溶于水中，因此水与烯烃的反应可能很难完成。通常使用强酸（例如硫酸）或汞盐（非常毒性）来实现。 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已经证明了这种催化剂是有效的）。该策略可能非常强大，因为可以将硼原子用于进一步的（水后）化学反应来构建复杂产物。这些新的反应策略将用于合成各种产品，包括感兴趣的分子以筛查医学研究中的疾病靶标。这将使我们能够与适当的生物学家建立合作，以便将我们的新发现应用于新的医疗治疗。

项目成果

期刊论文数量（9）

专著数量（0）

科研奖励数量（0）

会议论文数量（0）

专利数量（0）

Palladium(II)-Catalysed Oxidation of Alkenes

DOI：
10.1055/s-0035-1560465
发表时间：
2015-10-01
期刊：
SYNTHESIS-STUTTGART
影响因子：
2.6
作者：
Mann, Sam E.;Benhamou, L.;Sheppard, Tom D.
通讯作者：
Sheppard, Tom D.

Irreversible endo-selective diels-alder reactions of substituted alkoxyfurans: a general synthesis of endo-cantharimides.

DOI：
10.1002/chem.201406286
发表时间：
2015-04-13
期刊：
CHEMISTRY-A EUROPEAN JOURNAL
影响因子：
4.3
作者：
Foster, Robert W.;Benhamou, Laure;Porter, Michael J.;Bucar, Dejan-Kresimir;Hailes, Helen C.;Tame, Christopher J.;Sheppard, Tom D.
通讯作者：
Sheppard, Tom D.

Sustainable Synthesis of Chiral Tetrahydrofurans through the Selective Dehydration of Pentoses.