Multi-step reaction with 9 steps
1: 1.) n-BuLi, TMEDA, 2.) triisopropyl borate, 3.) tetrakis(triphenylphosphine)palladium, Na2CO3
2: 100 percent / Br2 / CCl4 / 0.67 h / 0 - 5 °C
3: 92 percent / aq. NaOH / methanol / 3 h / Heating
4: 18 percent / diphenylphosphorazidate, Et3N / dioxane / 20 h / Heating
5: 97 percent / NBS, benzoyl peroxide / CCl4 / 1.5 h / Heating; Irradiation
6: 62 percent / K2CO3 / dimethylformamide / 16 h / Ambient temperature
7: 32 percent / bis(triphenylphosphine)palladium dichloride, CuI, diethylamine / 29 h / 90 °C
8: 72 percent / aq. NaOH / methanol; tetrahydrofuran / 16 h / Ambient temperature
9: 88 percent / H2 / 10percent Pd/C / ethanol / 0.33 h / 760 Torr / Ambient temperature
With
bis-triphenylphosphine-palladium(II) chloride; sodium hydroxide; N-Bromosuccinimide; copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); n-butyllithium; Perbenzoic acid; Triisopropyl borate; N,N,N,N,-tetramethylethylenediamine; diphenyl phosphoryl azide; hydrogen; bromine; sodium carbonate; potassium carbonate; diethylamine; triethylamine;
palladium on activated charcoal;
In
tetrahydrofuran; 1,4-dioxane; methanol; tetrachloromethane; ethanol; N,N-dimethyl-formamide;
DOI:10.1021/jm00045a016