Cationic iron porphyrins with sodium dodecyl sulphate for micellar catalysis of cyclopropanation reactions.

Ruben V Maaskant,Roos C W Van Lier,Gerard Roelfes,Ehider A Polanco

doi:10.1039/c9ob02223f

Abstract

Here, we report that the combination of cationic iron porphyrins with sodium dodecyl sulphate (SDS) gives rise to efficient micellar catalysis of cyclopropanation reactions of styrene derivatives, using diazoacetates as carbene precursors. This simple, yet effective approach for cyclopropanations illustrates the power of micellar catalysis.

Highlights

We report that the combination of cationic iron porphyrins with sodium dodecyl sulphate (SDS) gives rise to efficient micellar catalysis of cyclopropanation reactions of styrene derivatives, using diazoacetates as carbene precursors
We report that the combination of cationic iron porphyrins with anionic surfactants, such as SDS, gives rise to efficient catalysis of cyclopropanation reactions of styrene derivatives
We have reported the micelle accelerated cationic iron porphyrin catalyzed cyclopropanation

Summary

Cationic iron porphyrins with sodium dodecyl

We report that the combination of cationic iron porphyrins with sodium dodecyl sulphate (SDS) gives rise to efficient micellar catalysis of cyclopropanation reactions of styrene derivatives, using diazoacetates as carbene precursors. We have reported on a DNA/cationic iron porphyrin hybrid that showed highly accelerated catalysis of cyclopropanation reactions.[11] It was proposed that the observed DNA-induced rate acceleration is due concentration of the reactants in hydrophobic spaces close to the DNA, resulting in a high effective molarity. This is reminiscent of micellar catalysis, where similar effects play a role. While all sodium alkyl sulphate surfactants accelerate the reaction above their CMCs, SDS proved to be the optimal surfactant for this reaction

Entry Catalyst Surfactant

Diazo reagent

Findings

Conflicts of interest