Multi-step reaction with 13 steps
1.1: copper(l) iodide; 1,10-Phenanthroline; caesium carbonate / toluene / 48 h / 100 °C / Inert atmosphere
2.1: trichlorophosphate / tetrahydrofuran / 3.75 h / 0 - 22 °C / Inert atmosphere
3.1: silver trifluoroacetate; iodine / tetrahydrofuran / 16 h / 0 - 22 °C / Inert atmosphere
4.1: bis-triphenylphosphine-palladium(II) chloride; sodium carbonate / acetonitrile; water / 48 h / 60 °C / Inert atmosphere
5.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 16 h / 0 - 22 °C / Inert atmosphere
6.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere
6.2: -78 °C / Inert atmosphere
7.1: platinum(IV) oxide hydrate; hydrogen / tetrahydrofuran / 48 h / 22 °C
8.1: tetrabutylammonium acetate; potassium carbonate; potassium chloride; palladium diacetate / N,N-dimethyl-formamide / 48 h / 100 °C / Inert atmosphere; Sealed tube
9.1: potassium hydroxide / tetrahydrofuran; water; ethanol / 24 h / 22 °C / Inert atmosphere
10.1: MoOPH / methanol / 16 h / 22 °C / Inert atmosphere
11.1: C34H12F14O2 / toluene / 48 h / 80 °C / Inert atmosphere; Molecular sieve; Sealed tube
12.1: Nitrosobenzene; D-Prolin / acetonitrile / 6 h / 4 °C / Inert atmosphere
12.2: 16 h / 22 °C / Inert atmosphere
13.1: trifluoroacetic acid / dichloromethane / 2 h / 22 °C / Inert atmosphere
13.2: 3 h / 22 °C / Inert atmosphere
With
bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; n-butyllithium; 1,10-Phenanthroline; platinum(IV) oxide hydrate; C34H12F14O2; potassium chloride; hydrogen; iodine; tetrabutylammonium acetate; palladium diacetate; silver trifluoroacetate; sodium carbonate; potassium carbonate; caesium carbonate; N-ethyl-N,N-diisopropylamine; Nitrosobenzene; trifluoroacetic acid; D-Prolin; potassium hydroxide; trichlorophosphate;
In
tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile;
1.1: |Ullmann-Goldberg Substitution / 2.1: |Vilsmeier-Haack Formylation / 4.1: |Suzuki-Miyaura Coupling / 6.1: |Wittig Olefination / 6.2: |Wittig Olefination / 8.1: |Heck Reaction;
DOI:10.1021/acs.joc.7b01192