1.1: palladium diacetate; sodium carbonate; triphenylphosphine / propan-1-ol; toluene / 4 h / Reflux; Inert atmosphere 2.1: N-hexadecyl-N,N,N-trimethylammonium bromide; potassium hydroxide / anhydrous xylene / 3 h / Reflux 2.2: 0.5 h / pH 1 / Reflux View Scheme

1.1: potassium carbonate / butanone / 8 h / Reflux 2.1: n-butyllithium / tert-butyl methyl ether / 2 h / -20 °C / Inert atmosphere 2.2: -60 - 20 °C 2.3: 0.17 h / 20 °C 3.1: palladium diacetate; sodium carbonate; triphenylphosphine / propan-1-ol; toluene / 4 h / Reflux; Inert atmosphere 4.1: N-hexadecyl-N,N,N-trimethylammonium bromide; potassium hydroxide / anhydrous xylene / 3 h / Reflux 4.2: 0.5 h / pH 1 / Reflux View Scheme

dicyclohexyl-carbodiimide in dichloromethane Ambient temperature;

1: dicyclohexylcarbodiimide / CH2Cl2 / Ambient temperature 2: dimethylformamide / Ambient temperature View Scheme