The Diels-Alder (DA) reaction is one the most widely used reactions to form C-C bonds in organic chemistry. However, the DA reactions between electronically mismatched partners are difficult to achieve thermally in traditional conditions. A few methods are able to perform this transformation using a radical cation strategy. But these approaches either give low yields of DA products or require the use of expensive materials or specialized setups. We have discovered an easy way to conduct Diels-Alder (DA) reactions at room temperature between electron-rich dienes and electron-rich dienophiles. The reaction gives excellent yields of DA products in a highly regio- and diastereoselective manner. This talk will discuss our efforts in developing this method and showcase our systematic research to investigate the reaction mechanism. The study of substrate scope will also be presented. This approach has the potential to become the most economical, sustainable, and practical method for the formation of DA products between electron-rich partners, thus making the electronically mismatched DA reactions much easier.

Novel approach to conduct electronically mismatched Diels-Alder reactions

2019 Spring National Meeting

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