Multi-step reaction with 8 steps
1.1: tributyl-amine; triphenyl-arsane; palladium diacetate / N,N-dimethyl-formamide / 15 h / 20 - 70 °C / Inert atmosphere
2.1: tetrabutyl ammonium fluoride / tetrahydrofuran; N,N-dimethyl-formamide / 2 h / 0 - 20 °C / Inert atmosphere
3.1: sodium triacetoxyborohydride; acetic acid / acetonitrile / 1 h / 0 °C / Inert atmosphere
4.1: pyridine / 2.15 h / 20 °C / Inert atmosphere
5.1: palladium 10% on activated carbon; hydrogen; triethylamine / ethyl acetate / 1 h / 20 °C / Inert atmosphere
6.1: tert.-butylhydroperoxide; potassium iodide / water; acetonitrile / 2 h / 75 °C / Darkness; Inert atmosphere
7.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere
8.1: trimethyl phosphite; N,N,N',N'-tetramethyl-1,8-diaminonaphthalene; trichlorophosphate / -15 - -10 °C / Inert atmosphere
8.2: 0.5 h / -10 °C / Inert atmosphere
With
pyridine; trimethyl phosphite; tert.-butylhydroperoxide; tributyl-amine; triphenyl-arsane; palladium 10% on activated carbon; sodium triacetoxyborohydride; tetrabutyl ammonium fluoride; hydrogen; palladium diacetate; N,N,N',N'-tetramethyl-1,8-diaminonaphthalene; acetic acid; triethylamine; potassium iodide; trichlorophosphate;
In
tetrahydrofuran; water; ethyl acetate; N,N-dimethyl-formamide; acetonitrile;
1.1: Heck reaction;
DOI:10.1002/chem.201102066