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.

含有碳-碳双键的简单有机分子（称为烯烃）是广泛使用的大宗化学品，可作为合成各种具有有用特性的更复杂分子（药物、精细化学品、农用化学品、聚合物等）的基本原料。在本提案中，我们概述了将烯烃直接转化为复杂分子结构的新催化策略。在每种情况下，通过在烯烃的碳-碳双键上正式加成水分子（水合反应）来引发一系列新颖的反应。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（例如硫酸）或汞盐（毒性很大）来实现。在这项研究中，我们将采用一种基于我们实验室之前工作的新策略，其中水分子附着在有机含硼化合物上，使其能够“溶解”在有机溶剂中，并在存在的情况下更容易发生反应合适的催化剂（在这个项目中，将使用基于钯、铂和金等金属的更高效、毒性更低的催化剂——我们的初步实验已经证明此类催化剂是有效的）。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）化学反应来构建复杂的产品。这些新的反应策略将用于合成多种产品，包括医学研究中用于筛选疾病靶点的感兴趣分子。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医学治疗的开发。

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.

Asymmetric Synthesis of Secondary Alcohols and 1,2-Disubstituted Epoxides via Organocatalytic Sulfenylation

有机催化亚磺酰化不对称合成仲醇和1,2-二取代环氧化物