Vinylcyclopropane [3+2] cycloaddition with acetylenic sulfones based on visible light photocatalysis

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Abstract

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.

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Chemistry - a European journal, 28, 18, Wiley-VCH, Weinheim, 2022, https://doi.org/10.1002/chem.202104329

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