Browsing by Author "Skumial, Piotr"

Now showing 1 - 1 of 1

Cu-catalyzed three-component carboamination of vinylcyclopropanes
(2024-05) Skumial, Piotr ; Hull, Kami; Anslyn, Eric V.
This thesis introduces and explores the expanding field of applications for three-membered carbocycles, which has seen a resurgence recently. Traditionally, the utility of these small rings in organic chemistry was largely shown in radical clock experiments for elucidating reaction mechanisms. However, the past decades has seen their use broaden significantly due to advances in transition metal catalysis. Three-membered carbocycles, such as cyclopropenes, methylenecyclopropanes, vinylcyclopropanes, and cyclopropanes, are crucial for constructing complex molecular architectures due to their unique structural and electronic properties. These characteristics facilitate a diverse array of chemical transformations, making them versatile building blocks in synthetic chemistry. This work is devoted to the development of vinylcyclopropane chemistry, with a focus on the copper-catalyzed procedure that enable regioselective ring-opening and 1,5-carboamination difunctionalizations. These methodologies are crucial for the efficient construction of nitrogen-containing organic compounds, which are key in the development of pharmaceuticals, agrochemicals, and functional materials. A broad substrate scope with good functional group tolerance is demonstrated. Additionally, mechanistic insights of the reaction are discussed.