Development of Practical Electron Transfer Driven Reactions for Organic Synthesis

实用电子转移驱动有机合成反应的发展

• 批准号: 11555242
• 负责人: YOSHIDA Jun-ichi
• 金额: $ 8.64万
• 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: 1999
• 资助国家: 日本
• 起止时间: 1999 至 2001
• 项目状态: 已结题
• 来源: https://kaken.nii.ac.jp/en/grant/KAKENHI-PROJECT-11555242/
• 关键词: Electron Transfer; Cation Pool Method; Cation Flow Method; Combinetorial Synthesis; 電子移動駆動型反応; 炭素カチオン; 炭素求核剤; 炭素-炭素結合形成; 炭素―炭素結合形成

We aimed to develop a practical electron transfer driven reaction for organic synthesis, and a "cation flow"method has been developed on the basis of the "cation pool" method. In the "cation flow" method, carbocations generated using a low temperature electrochemical microflow reactor were immediately trapped with carbon nucleophies. Downsizing of a electrochemical flow reactor enables efficient temperature control and shortening ofa residence time, and thus an application of this system to less stable carbocation could be possible. We have also developed a direct analysis system of the flow of the carbocations using FITR spectrometer. More outstanding feature of the "cation flow" system is that continuous sequential combinatorial synthesis can be accomplished by simple flow switching. Although parallel syntheses enjoy versatile applications in combinatorial chemistry, the present continuous sequential method opens a new intriguing aspect of combinatorial synthesis.

为了发展一种实用的电子转移驱动的有机合成反应，在“阳离子池”方法的基础上发展了“阳离子流”方法。在“阳离子流”方法中，使用低温电化学微流反应器产生的碳阳离子立即被碳亲核体捕获。电化学流动反应器的小型化使得能够有效地控制温度并缩短停留时间，因此该系统可以应用于不太稳定的碳正离子。我们还开发了一个使用FITR光谱仪的碳阳离子流动的直接分析系统。“阳离子流”系统更突出的特点是通过简单的流路切换就可以实现连续的顺序组合合成。虽然平行合成在组合化学中有着广泛的应用，但目前的连续序贯方法为组合合成开辟了一个新的有趣的方面。

项目成果

Jun-ichi Yoshida: "Electron Transfer Driven Organic Reactions""New Trends in Synthetic Organic Chemistry" Kikankagakusousetsu. 47. 138-148 (2000)

Jun-ichi Yoshida：“电子转移驱动的有机反应”“合成有机化学的新趋势”Kikankagakusousetsu。

Jun-ichi Yoshida: ""Cation Flow" Method. A New Approach to Conventional and Combinatorial Organic Syntheses Using Electrochemical Microflow Systems"Journal of the American Chemical Society. 123. 7941-7942 (2001)

Jun-ichi Yoshida：““阳离子流”方法。使用电化学微流系统进行常规和组合有机合成的新方法”美国化学会杂志。

Jun-ichi Yoshida: "Cation Pool Method. Accumulation and Reactions of Reactive Carbocation Intermediate"Gendaikagaku. 7. 36 (2001)

Jun-ichi Yoshida：“阳离子池法。反应性碳阳离子中间体的积累和反应”现代化学。

Jun-ichi Yoshida: "Reaction of electrogenerated "Iminium Cation Pool" with organometallic Reagents. Direct Oxidative α-Alkylation and -Arylation of Amine Derivatives"Tetrahedron Letters. 42. 2173-2176 (2001)

Jun-ichi Yoshida：“电化学“亚胺阳离子池”与有机金属试剂的反应。胺衍生物的直接氧化 α-烷基化和-芳基化”Tetrahedron Letters 42。2173-2176 (2001)

Jun-ichi Yoshida: "Reaction of Electrogenerated "Irainium Cation Pool" with Organometal lie Reagents. Direct Oxidative a-Alkylation and -Arylation of Araine Derivatives"Tetrahedron Letters. 42. 2173-2176 (2001)

Jun-ichi Yoshida：“电生成的“Irainium阳离子池”与有机金属试剂的反应。Araine衍生物的直接氧化α-烷基化和-芳基化”四面体字母。