The Development of Carbon-Carbon Bond Forming Process Using Aluminum Metal as A Electron Pool

金属铝是一个电子池(还原剂)，涉及大量的反应电子。我们已经证明，通过一种以铝为电子源的新的电子转移过程，可以选择性地实现官能团的多样化转化和碳-碳键的形成反应。在这个项目中，为了开发实用的工艺，我们研究了以下基本课题：(A)金属铝表面的电子转移过程高度依赖于溶剂、另一种氧化还原金属和添加剂。我们研究了双金属氧化还原体系，以实现最有效的电子转移体系。(B)一些由过渡金属、还原金属和电子池金属组成的多金属氧化还原体系已经被发现实现了各种涉及碳-碳键形成的有机反应。作为例子，开发了一种由卤代烯烃生成二烯的简便偶联反应。(C)将氧化还原体系应用于β-内酰胺类化合物的转化，开发了新的实用的抗生素合成工艺。

Aluminum metal is an electron pool (reducing agent) which involves a lot of reactive electrons. We have demonstrated that a diverse transformation of functional groups and carbon-carbon bond forming reactions are selectively achieved by a new electron transfer process using aluminum metal as an electron source. In this project, we have investigated the following fundamental subjects in order to develop practical processes.(a) The electron transfer process from the surface of aluminum metal is highly dependent on the solvent, another redox metal, and additives. We have studied the bimetal redox system to realize the most efficient electron transfer system for the purposes.(b) Some multi metal redox systems consisting of transition metal, reducing metal, and electron pool metal have been found to achieve a variety of organic reactions involving carbon-carbon bond formation. As an example, a facile coupling reaction of alkenyl halides leading to dienes was developed.(c) The redox systems have been applied to the transformation of beta-lactam compounds and new practical synthetic processes of the antibiotics have been developed.