1H-imidazole; iodine; triphenylphosphine in tetrahydrofuran T=20°C; Inert atmosphere;

4-methyl-benzoic acid methyl ester; tetra-n-butylammonium tetrafluoroborate in N,N-dimethyl-formamide T=60°C; 6 h; ElectrolysisInert atmosphere;

1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide 2: diethyl ether 3: sodium hydride / tetrahydrofuran 4: 2,2'-azo-bisisobutyronitrile; tri-n-butyl-tin hydride / toluene 5: dichloro bis(acetonitrile) palladium(II); oxygen; copper(l) chloride / water; N,N-dimethyl-formamide View Scheme

1: 2,6-dimethylpyridine / dichloromethane / 0.25 h / -78 °C / |Inert atmosphere 2: (N,N'-bis(2,6-diisopropylphenyl)imidazol-2-ylidene)CuOtBu; 1,1,3,3-tetramethyldisiloxane; cesium fluoride / 1,4-dioxane / 4 h / 25 °C / |Glovebox; |Inert atmosphere View Scheme