Multi-step reaction with 14 steps
1: sodium tetrahydroborate; cerium(III) chloride heptahydrate / methanol / 4 h / -20 - 0 °C / Inert atmosphere
2: dmap; triethylamine / dichloromethane / 1 h / 0 °C / Inert atmosphere
3: palladium diacetate; triethylamine; triphenylphosphine / toluene / 3.33 h / 25 - 110 °C / Inert atmosphere
4: oxygen; 5,15,10,20-tetraphenylporphyrin / dichloromethane / 24 h / 25 °C / Inert atmosphere; UV-irradiation
5: thiourea / methanol / 2 h / 25 °C / Inert atmosphere
6: triethylamine / dichloromethane / 1.5 h / 0 °C / Inert atmosphere
7: toluene / 3 h / 110 °C / Inert atmosphere
8: phosphorous acid trimethyl ester / 16 h / 111 °C / Inert atmosphere
9: hydrogenchloride / diethyl ether; dichloromethane / 0.25 h / 0 °C / Inert atmosphere
10: trifluoroacetic acid / dichloromethane / 4 h / 0 - 25 °C / Inert atmosphere
11: N-ethyl-N,N-diisopropylamine / dichloromethane / 17 h / 0 - 25 °C / Inert atmosphere
12: tris-(dibenzylideneacetone)dipalladium(0); diethylamine; 1,4-di(diphenylphosphino)-butane / tetrahydrofuran / 2.05 h / 25 °C / Inert atmosphere
13: sulfur; lithium hexamethyldisilazane / tetrahydrofuran; diethyl ether / 5 h / 25 °C / Inert atmosphere
14: dmap; dicyclohexyl-carbodiimide / dichloromethane / 5 h / 0 - 25 °C / Inert atmosphere
With
hydrogenchloride; sulfur; dmap; sodium tetrahydroborate; tris-(dibenzylideneacetone)dipalladium(0); cerium(III) chloride heptahydrate; oxygen; palladium diacetate; 5,15,10,20-tetraphenylporphyrin; diethylamine; triethylamine; N-ethyl-N,N-diisopropylamine; thiourea; dicyclohexyl-carbodiimide; triphenylphosphine; 1,4-di(diphenylphosphino)-butane; trifluoroacetic acid; lithium hexamethyldisilazane; phosphorous acid trimethyl ester;
In
tetrahydrofuran; methanol; diethyl ether; dichloromethane; toluene;
1: |Luche Cerium Reduction;
DOI:10.1021/ja308429f