Iron-catalyzed spirocyclization project

Michalska, Weronika and Sweeney, Joe (2020) Iron-catalyzed spirocyclization project. Masters thesis, Lancaster University.

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Abstract

This project focuses on iron-catalysed heterospirocyclization reactions of aryl iodide substrates using Grignard reagents. Specifically, alkyl Grignard reagents were used, in an extension to previous work using aryl Grignard reagents. The first stage of the project included the formation of heterospirocycles from 2-[(2-iodophenoxy)methyl]-furan (X=O) in the presence of alkyl Grignard reagents. Optimisation of the reaction was not successful, but yielded six novel heterospirocycles in low yield (5-35 %). Next, new amine (X=N) systems were designed to undergo the spirocyclization reaction. However, none of the pathways were successful. Thirdly, the project included the design and synthesis of novel vinyl iodide reagents. The vinyl iodine reagent underwent the spirocyclization reaction in the presence of phenylmagnesium bromide (PhMgBr) to yield five novel heterospirocycles in 5-50% yield.