pyridine hydrogenfluoride; sodium nitrite T=0 - 50°C; 1.5 h;

C94H134O4P2Pd2; cesium fluoride in toluene T=130°C; 14 h; Inert atmosphere;

in diethyl ether 1.) 0 deg C, 2.) RT, overnight;

1: |Inert atmosphere 2: cesium fluoride; C94H134O4P2Pd2 / toluene / 14 h / 130 °C / |Inert atmosphere View Scheme

1: 27 percent / potassium permanganate / H2O / 1.) from RT to 43 deg C, 5 h, 2.) 45 deg C, overnight 2: thionyl chloride / Heating 3: ammonia gas / 1,2-dichloro-ethane / 0.5 h / -30 °C 4: 67 percent / bromine, aq. potassium hydroxide / 1.) RT, 1 h, 2.) 70 deg C, 15 min 5: 1.) 48-50percent fluoroboric acid, isoamyl nitrite / 1.) ethanol, -10 deg C, 20 min, 2.) a.) hexane, from 0 deg C to RT, b.) reflux, 30 min 6: 66 percent / potassium permanganate / H2O / 3 h / Heating 7: 99 percent / diethyl ether / 1.) 0 deg C, 2.) RT, overnight View Scheme

1: 66 percent / potassium permanganate / H2O / 3 h / Heating 2: 99 percent / diethyl ether / 1.) 0 deg C, 2.) RT, overnight View Scheme

1: 1.) 48-50percent fluoroboric acid, isoamyl nitrite / 1.) ethanol, -10 deg C, 20 min, 2.) a.) hexane, from 0 deg C to RT, b.) reflux, 30 min 2: 66 percent / potassium permanganate / H2O / 3 h / Heating 3: 99 percent / diethyl ether / 1.) 0 deg C, 2.) RT, overnight View Scheme

1: thionyl chloride / Heating 2: ammonia gas / 1,2-dichloro-ethane / 0.5 h / -30 °C 3: 67 percent / bromine, aq. potassium hydroxide / 1.) RT, 1 h, 2.) 70 deg C, 15 min 4: 1.) 48-50percent fluoroboric acid, isoamyl nitrite / 1.) ethanol, -10 deg C, 20 min, 2.) a.) hexane, from 0 deg C to RT, b.) reflux, 30 min 5: 66 percent / potassium permanganate / H2O / 3 h / Heating 6: 99 percent / diethyl ether / 1.) 0 deg C, 2.) RT, overnight View Scheme

1: 67 percent / bromine, aq. potassium hydroxide / 1.) RT, 1 h, 2.) 70 deg C, 15 min 2: 1.) 48-50percent fluoroboric acid, isoamyl nitrite / 1.) ethanol, -10 deg C, 20 min, 2.) a.) hexane, from 0 deg C to RT, b.) reflux, 30 min 3: 66 percent / potassium permanganate / H2O / 3 h / Heating 4: 99 percent / diethyl ether / 1.) 0 deg C, 2.) RT, overnight View Scheme

1: ammonia gas / 1,2-dichloro-ethane / 0.5 h / -30 °C 2: 67 percent / bromine, aq. potassium hydroxide / 1.) RT, 1 h, 2.) 70 deg C, 15 min 3: 1.) 48-50percent fluoroboric acid, isoamyl nitrite / 1.) ethanol, -10 deg C, 20 min, 2.) a.) hexane, from 0 deg C to RT, b.) reflux, 30 min 4: 66 percent / potassium permanganate / H2O / 3 h / Heating 5: 99 percent / diethyl ether / 1.) 0 deg C, 2.) RT, overnight View Scheme