toluene-4-sulfonic acid in dichloromethane T=0 - 20°C; 2.5 h;

pyridinium p-toluenesulfonate in dichloromethane

TBBDA T=20°C; 0.1 h; Neat (no solvent);

2,2'-azo-bisisobutyronitrile; tris-(trimethylsilyl)silane

silica triflate in methanol 0.0833333 h; Heating;

dipotassium peroxodisulfate; β-MoO3 in water; acetonitrile 1.5 h; Reflux;

1.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C 1.2: -78 - 20 °C 2.1: toluene-4-sulfonic acid / methanol / 16 h / 20 °C 3.1: tetrahydrofuran; diethyl ether / 4 h / -78 - 20 °C 4.1: biphenyl-2-yl-di-tert-butyl-phosphane; lithium tert-butylate; [(Mes)Cu]n / 1,4-dioxane / 4 h / 20 °C View Scheme

1: 1) Mg; 2) CuI / 1) THF, reflux, 3 h, 2) THF, room temp., 15 h 2: 92 percent / p-toluenesulfonic acid (p-TsOH) / methanol / 6 h / Heating View Scheme

1: n-butyllithium 2: methanol / Acidic conditions 3: tetrahydrofuran View Scheme

1.1: n-butyllithium / diethyl ether; hexane / 3.5 h / -78 °C / |Inert atmosphere 1.2: 20 °C / |Inert atmosphere 2.1: potassium carbonate; bis(η3-allyl-μ-chloropalladium(II)); dicyclohexyl(2',6'-diisopropoxy-[1,1'-biphenyl]-2-yl)phosphine; copper(l) iodide / N,N-dimethyl-formamide; tetrahydrofuran / 24 h / 80 °C / |Inert atmosphere 3.1: toluene-4-sulfonic acid / methanol / 16 h / 20 °C / |Inert atmosphere View Scheme