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Trimethylenemethane Reactions

  • Team: Tian Li, Kiet Pham
  • Goal: To generate the trimethylenemethane intermediate and have it react with various radical quenchers intra- and intermolecularly. When the methodology is developed beyond a proof of concept, the reactions will be applied to the targeted synthesis of a biologically active molecule.
  • Summary: In this project, a hypervalent iodonium alkynyl triflate (HIAT) will be used to generate a reactive vinylidene carbene intermediate. The vinylidene carbene will then react intramolecularly with an alkene to temporarily form a trimethylenemethane (TMM) diyl. Depending on the initial HIAT and the nucleophile involved with the reaction, an array of fused ring structures can be formed. The mechanism of TMM diyls is understood but there are limited studies using HIATs to generate them and most only use them for [3+2] cycloadditions. The work will include reactivity studies, investigation functional group tolerance, and explore interesting ring structures made possible by this methodology.