Multi-step reaction with 17 steps
1.1: C49H37Cl2IrN2O6P2; potassium phosphate / tetrahydrofuran / 144 h / 55 °C / Sealed tube; Inert atmosphere
2.1: diethyl ether / 1 h / -78 - -20 °C / Inert atmosphere
3.1: pyridinium p-toluenesulfonate / tetrahydrofuran / 2.5 h / 50 °C / Inert atmosphere
4.1: Wilkinson's catalyst; hydrogen / dichloromethane / 3 h / 20 °C / 15001.5 Torr
5.1: ozone / dichloromethane / -78 °C
5.2: 20 °C / Inert atmosphere
5.3: 0 - 20 °C / Inert atmosphere
6.1: pyridinium p-toluenesulfonate; dihydrogen peroxide / acetonitrile; water / 1 h / 20 °C / Inert atmosphere
7.1: methanol / 20 °C / Inert atmosphere
7.2: 20 °C / Inert atmosphere
8.1: potassium carbonate / methanol / 20 h / 20 °C / Inert atmosphere
9.1: palladium diacetate; copper dichloride / 1,2-dichloro-ethane / 0.25 h / 20 °C / Molecular sieve; Inert atmosphere
9.2: 24 h / 20 - 40 °C / Inert atmosphere
10.1: lithium diisopropyl amide / tetrahydrofuran / -78 °C / Inert atmosphere
11.1: dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere
11.2: 20 °C / Inert atmosphere
12.1: pyridine hydrofluoride / 2 h / 0 - 20 °C / Inert atmosphere
13.1: acetone / 0.33 h / 20 °C / UV-irradiation; Inert atmosphere
14.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.5 h / -78 °C / Inert atmosphere
14.2: 0.33 h / -78 - 20 °C / Inert atmosphere
15.1: tetrahydrofuran; toluene / -78 - 20 °C / Inert atmosphere
16.1: acetic acid; tetrabutyl ammonium fluoride / tetrahydrofuran; toluene / 1 h / 20 °C / Inert atmosphere
17.1: pyrrolidine; copper(l) iodide; tetrakis(triphenylphosphine) palladium(0) / toluene / 4 h / 20 °C / Inert atmosphere
With
pyrrolidine; potassium phosphate; copper(l) iodide; Wilkinson's catalyst; tetrakis(triphenylphosphine) palladium(0); oxalyl dichloride; pyridine hydrofluoride; C49H37Cl2IrN2O6P2; tetrabutyl ammonium fluoride; hydrogen; dihydrogen peroxide; palladium diacetate; pyridinium p-toluenesulfonate; potassium carbonate; ozone; acetic acid; dimethyl sulfoxide; copper dichloride; lithium diisopropyl amide;
In
tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; 1,2-dichloro-ethane; acetone; toluene; acetonitrile;
14.1: |Swern Oxidation / 14.2: |Swern Oxidation / 17.1: |Sonogashira Cross-Coupling;
DOI:10.1021/jacs.7b13591