GoKawiilThianthrenium ylides enable carbene transfer for cyclopropanation reactions
Researchers report that thianthrenium ylides can act as effective carbene donors for cyclopropanation, a reaction where conventional sulfonium and sulfoxonium salts have largely failed. They attribute this failure in prior chemistry to strong carbon-sulfur bonding in typical sulfur ylides, which prevents formation of a sufficiently electrophilic metal-carbene intermediate needed for broad olefin reactivity.
GoKawiil's interpretation of the reporting above, not reported fact.
This work suggests a new class of reagents could expand the scope of carbene-transfer chemistry beyond the electron-rich olefins that have limited existing sulfonium- and diazo-based methods. If thianthrenium ylides prove broadly applicable, they could offer chemists a more versatile and potentially safer alternative to diazoacetates for building cyclopropane rings, which are common motifs in pharmaceuticals and agrochemicals.
- Thianthrenium ylides are introduced as viable carbene donors for cyclopropanation
- Conventional sulfonium/sulfoxonium salts largely failed due to strong carbon-sulfur interactions limiting carbene electrophilicity
- The approach may broaden the range of olefins accessible to iron-catalyzed carbene-transfer cyclopropanation
Source: nature.com — Behera, 2026-09-30
Published there as: “Carbene transfer from thianthrenium ylides for cyclopropanation”
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