Metal catalyzed carbene transfer reactions occurring through carbenoid processes encompass a vast array of reactants and catalysts to achieve novel and selective strategies for synthesis. However, they are often mediated by expensive precious metal catalysts (e.g. rhodium, ruthenium, palladium, gold), which become a major obstacle to the synthesis of enantiopure compounds in an economical fashion. Iron is the second most abundant metal on the earth, its application in catalytic carbene transfers is underdeveloped. In this research, we report here the first bis(imino)pyridine iron catalyzed cyclopropanation reaction of donor-acceptor diazo compounds. The <i>N</i>-aryl substituted bis(imino)pyridine iron catalysts exhibit high catalytic activity towards the cyclopropanation reaction of various diazoacetates and styrene with up to 85% yield. A series of chiral bis(imino)pyridine iron catalysts are also synthesized and their activity and selectivity in asymmetric cyclopropanation reaction are under investigation. This project will deliver a new type of iron catalysts for the catalytic carbene transfer reactions, which will promote the construction of molecular complexity in a more eco- and environmentally friendly approach.

Catalytic bis(imino)pyridine iron complexes for carbene reactions of diazo compounds

2019 Spring National Meeting

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.