Vinylcyclopropane [3+2] Cycloaddition with Acetylenic Sulfones Based on Visible Light Photocatalysis**
Adriana Luque, Jonathan Groß, Till J. B. Zähringer, Christoph Kerzig, Till Opatz
Abstract
The first intermolecular visible light [3+2] cycloaddition reaction performed on a meta photocycloadduct employing acetylenic sulfones is described. The developed methodology exploits the advantages of combining UV and visible-light in a two-step sequence that provides a photogenerated cyclopropane which, through a strain-release process, generates a new cyclopentane ring while significantly increasing the molecular complexity. Mechanistic studies and DFT calculations indicate an energy transfer pathway for the visible light-driven reaction step. This strategy could be extended to simpler vinylcyclopropanes.
Topics & Concepts
CycloadditionCyclopentaneCyclopropaneVisible spectrumPhotochemistryPhotocatalysisIntermolecular forceRing (chemistry)ChemistryMaterials scienceMoleculeStereochemistryCatalysisOrganic chemistryOptoelectronicsSulfur-Based Synthesis TechniquesRadical Photochemical ReactionsCatalytic Alkyne Reactions