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Updated: Mar 10, 2026

Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes
Published on: September 8, 2013
Recyclable Hypervalent-Iodine-Mediated Dehydrogenative Cyclopropanation under Metal-Free Conditions
Ya-Nan Duan1, Zhao Zhang1, Chi Zhang1
1State Key Laboratory of Elemento-Organic Chemsitry, Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Nankai University , Tianjin 300071, P. R. China.
Abstract:
A method is developed for the synthesis of cyclopropanes from the C(sp2)-C(sp3) single bonds of β-keto esters with activated methylene compounds under metal-free conditions in the presence of 5-trimethylammonio-1,3-dioxo-1,3-dihydro-1λ5-benzo[d][1,2]iodoxol-1-ol anion (AIBX), a recyclable water-soluble hypervalent iodine(V) reagent developed by our group. This mild, efficient method has a wide substrate scope and good functional group tolerance and is complementary to existing cyclopropanation strategies. The method can be used to construct polysubstituted ring-fused cyclopropanes and is amenable to further synthetic transformations for construction of complex biologically active molecules as well as asymmetric cyclopropanes (90% de) when a chiral ester auxiliary is used.
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