Multi-step reaction with 11 steps
1.1: trifluoroacetic acid / dichloromethane / 2 h / 23 °C / Inert atmosphere
1.2: 2 h / 0 - 23 °C / Molecular sieve; Inert atmosphere
2.1: trifluoroacetic acid / dichloromethane / 1 h / 23 °C / Inert atmosphere
2.2: 18 h / 0 - 23 °C / Inert atmosphere
3.1: boron trifluoride diethyl etherate / acetonitrile / 0.33 h / 0 °C / Inert atmosphere
3.2: 0.83 h / 0 °C / Inert atmosphere
4.1: N-chloro-succinimide; titanium tetrachloride / dichloromethane; acetonitrile / 15 h / 23 °C / Inert atmosphere
5.1: water; silver hexafluoroantimonate / nitromethane / 2 h / 23 °C / Inert atmosphere
6.1: 2,6-dimethylpyridine / dichloromethane / 35 h / 23 °C / Inert atmosphere
7.1: palladium diacetate; triethylsilane; triethylamine / dichloromethane / 3.5 h / 23 °C / Inert atmosphere
8.1: silver hexafluoroantimonate; 2,6-di-tert-butyl-4-methylpyridine / 0.67 h / 23 °C / Inert atmosphere
9.1: palladium 10% on activated carbon; ammonium formate / ethanol / 20 h / 70 °C / Inert atmosphere
10.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 23 °C / Inert atmosphere
11.1: triethylsilane; methanesulfonic acid / dichloromethane / 4 h / 23 °C / Inert atmosphere
With
2,6-dimethylpyridine; triethylsilane; N-chloro-succinimide; silver hexafluoroantimonate; 2,6-di-tert-butyl-4-methylpyridine; methanesulfonic acid; palladium 10% on activated carbon; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; water; ammonium formate; palladium diacetate; titanium tetrachloride; triethylamine; trifluoroacetic acid;
In
tetrahydrofuran; nitromethane; ethanol; dichloromethane; acetonitrile;
8.1: |Friedel-Crafts Alkylation;
DOI:10.1021/jacs.5b12392