Multi-step reaction with 6 steps
1: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; triethylamine / tetrahydrofuran / 21 h / 45 °C / Inert atmosphere
2: bis(η3-allyl-μ-chloropalladium(II)); 1,1,1,2,2,2-hexamethyldisilane; water; triphenylphosphine / N,N-dimethyl acetamide / 15 h / 80 °C / Inert atmosphere
3: 1,3-bis(dicyclohexylphosphino)propane bis(tetrafluoroborate) salt; palladium diacetate; potassium carbonate / dimethyl sulfoxide / 20 h / 120 °C / Molecular sieve
4: boron tribromide / hexane; dichloromethane / -78 - 20 °C / Inert atmosphere
5: water / hexane; dichloromethane / 0 °C
6: potassium hydroxide / ethanol / 5 h / Reflux
With
bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; bis(η3-allyl-μ-chloropalladium(II)); 1,3-bis(dicyclohexylphosphino)propane bis(tetrafluoroborate) salt; 1,1,1,2,2,2-hexamethyldisilane; water; palladium diacetate; boron tribromide; potassium carbonate; triethylamine; triphenylphosphine; potassium hydroxide;
In
tetrahydrofuran; ethanol; hexane; dichloromethane; N,N-dimethyl acetamide; dimethyl sulfoxide;
2: Shirakawa-Hayashi reduction;
DOI:10.1021/jo300746x