sec.-butyllithium in tert-butyl methyl ether T=-18 - -5°C; 2.08333 h;

1: N-bromosuccinmide; 2,2'-azo-bisisobutyronitrile / benzene / 16 h / Reflux; Inert atmosphere 2: sulfuric acid / 3 h / 60 °C / Inert atmosphere 3: caesium carbonate; triphenylphosphine; palladium dichloride / tetrahydrofuran; water / 22 h / 85 °C / sealed tube; Inert atmosphere 4: bis(1,5-cyclooctadiene)-rhodium(I) tetrafluoroborate; 6-diphenylphosphinomethyl-3-methyl-2-aminopyridine / toluene / 1 h / 150 °C / Inert atmosphere View Scheme

nitric acid

1.1: 85 percent / Pd(PPh3)4; aq. Na2CO3 / 1,2-dimethoxy-ethane / Heating 2.1: 96 percent / LDA / tetrahydrofuran / 1 h / 20 °C 3.1: n-BuLi / tetrahydrofuran; hexane / 0.08 h / 0 °C 3.2: 90 percent / tetrahydrofuran; hexane / 0 - 20 °C 4.1: 68 percent / aq. HCO2H; Pd(OAc)2; Ph3P / dimethylformamide / 60 - 70 °C View Scheme

1: N-bromosuccinmide; dibenzoyl peroxide / chloroform / 8 h / 60 °C / Inert atmosphere 2: ethanol / 8 h / Reflux 3: copper(l) iodide; N-acetyl-glycine; potassium iodide; sodium hydroxide / tert-butyl alcohol / 18 h / 100 °C View Scheme

{C6H3[NHP(piperidinyl)2]2Pd(Cl)}; potassium carbonate in 1,4-dioxane; water; butan-1-ol T=100°C; Suzuki-Miyaura reaction; 6 h;

1: HNO3 2: PCl5 / 130 - 140 °C View Scheme