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Generations and Reactions of Reactive Organic Cations Using Flow Redox Systems

使用流动氧化还原系统的反应性有机阳离子的生成和反应

基本信息

批准号：
15350056
负责人：
SUGA Seiji
金额：
$ 9.79万
依托单位：
KYOTO UNIVERSITY
依托单位国家：
日本
项目类别：
Grant-in-Aid for Scientific Research (B)
财政年份：
2003
资助国家：
日本
起止时间：
2003 至 2005
项目状态：
已结题

项目摘要

Recently we have developed the "cation pool" method, which involves generation of highly reactive carbocations by low temperature electrolysis followed by reactions with a variety of nucleophiles. Micro flow reactors have received significant interest in the stream of downsizing of chemistry, and they are expected to make an innovative and revolutionary change for chemical synthesis. The advantages of microflow reactors of easy modulation and the possibility of combining reactors are quite useful to construct flow type redox systems for the organic transformations. On the basis of this concept we have developed "cation flow" method using microflow electrochemical reactors, which involves generation of highly reactive carbocations by low temperature electrolysis. This method enables the manipulation of carbocation intermediates to achieve direct oxidative C-C bond formation. Based on the "cation flow" method, continuous sequential combinatorial synthesis can be accomplished by simple flow switching. As an extension of the "cation flow" method, an electrochemical paired micro flow system that involves concurrent anodic generation of carbocations and cathodic generation of carbon nucleophiles followed by their reactions to achieve straightforward C-C bond formation has been developed. Anodic methoxylation of several organic compounds have also been achieved in the absence of intentionally added supporting electrolyte using an electrochemical microflow system.

最近，我们开发了“阳离子池”方法，该方法包括通过低温电解产生高活性碳阳离子，然后与各种亲核试剂反应。微流反应器在化学合成的小型化趋势中受到了极大的关注，并有望为化学合成带来创新性和革命性的变化。微流反应器的优点是易于调节和组合反应器的可能性是非常有用的，以构建流动型氧化还原系统的有机转化。在此基础上，我们已经开发了“阳离子流”的方法，使用微流电化学反应器，它涉及到生成高活性碳阳离子的低温电解。该方法使得能够操纵碳阳离子中间体以实现直接氧化C-C键形成。基于“阳离子流”方法，通过简单的流路切换，可以实现连续的顺序组合合成。作为“阳离子流”方法的延伸，已经开发了电化学成对微流系统，该系统涉及碳阳离子的同时阳极生成和碳亲核试剂的阴极生成，随后通过它们的反应来实现直接的C-C键形成。几种有机化合物的阳极甲氧基化也已经在没有有意添加的支持电解质的情况下使用电化学微流系统实现。