SOMOphilic Alkynylation of Unreactive Alkenes Enabled by Iron-Catalyzed Hydrogen Atom Transfer

We report an efficient and practical iron-catalyzed hydrogen atom transfer protocol for assembling acetylenic motifs into functional alkenes. Diversities of internal alkynes could be obtained from readily available alkenes and acetylenic sulfones with excellent Markovnikov selectivity. An iron hydride hydrogen atom transfer catalytic cycle was described to clarify the mechanism of this reaction.

Vinylcyclopropane [3+2] Cycloaddition with Acetylenic Sulfones Based on Visible Light Photocatalysis

We describe the first intermolecular visible light [3+2] cycloaddition reaction being performed on a meta photocycloadduct employing acetylenic sulfones. 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 increasing significally the molecular complexity. This strategy could be extended to simpler vinylcyclopropanes.

Direct and Efficient Synthesis of Sulfonium Acyl Sulfonylmethylide Ylides from Acetylenic Sulfones and Dimethyl Sulfoxide

Bifunctionalized sulfonium ylides, sulfonium acyl sulfonyl methylides, were directly and efficiently prepared from various acetylenic sulfones and aliphatic sulfoxides under heating conditions. The current method features short reaction time, low cost, readily available starting materials, convenient operation and purification, providing an efficient access to widely applied bifunctionalized sulfonium ylides.

SOMOphilic Alkynylation Using Acetylenic Sulfones as Functional Reagents

The past decades have witnessed a boom in alkynylation mainly owing to the importance of alkynyl-containing molecules in organic synthesis, drug discovery, polymer chemistry, and materials science. Besides conventional strategies,...