Accessing CF 3 -Cyclopropenes ─ A Platform for the Synthesis of Trifluoromethylated Building Blocks

2026/03/18 by Wei Wu, Tobias M. Milzarek, Matthew D. Wodrich +1 · 1 voice
Chemistry · Pharmacology, Toxicology and Pharmaceutics · #Cyclopropane Reaction Mechanisms #Fluorine in Organic Chemistry #Synthesis and Reactivity of Heterocycles

paper · doi:10.1021/acs.orglett.6c00410

openalex publication_date 2026/03/18 · openalex created_date 2026/03/20 · openalex updated_date 2026/07/22

Abstract

Cyclopropenes are the smallest unsaturated carbocycles. They possess exceptionally high ring strain, resulting in unique reactivity, enabling C═C bond functionalization and ring-opening transformations. Herein, we report a copper-mediated trifluoromethylation of cyclopropenyl benziodoxole (CpBX) reagents, providing access to previously inaccessible, yet highly useful, sp 2 -trifluoromethylated cyclopropenes. Subsequent functionalizations of these novel strained ring building blocks enable access to highly substituted trifluoromethylated cyclopropanes, difluoromethylene cyclopropanes and noncyclic trifluoromethylated compounds.

Citations

• Contribution of Organofluorine Compounds to Pharmaceuticals

Discussions

• The work of Josh, Tobias and Matthew on the synthesis of CF3-cycloproprenes using hypervalent iodine reagents and Cu(III) complexes is now published in Org. Lett. doi.org/10.1021/acs.... [bsky, 6 points, 0 comments]

Related

• Copper‐Catalyzed Cyclopropenation of Alkynes with Difluoromethyl Carbene†
• Divergent Mono‐ and Di‐trifluoromethylthiolation of Bicyclo[1.1.0]butane and Bicyclo[2.1.0]pentane†
• Recent Progresses towards the Strengthening of Cyclopropene Chemistry
• Synthesis of gem-difluorocyclobutanes: Organolanthanum enabled synthesis and divergent catalytic functionalization of gem-difluorocyclobutanols
• Selective Carbon–Carbon Bond Cleavage of Cyclopropanols