lithium tert-butylate; 2-(dicyclohexylphosphino)-2',4',6'-tri-i-propyl-1,1’-biphenyl; tris-(dibenzylideneacetone)dipalladium(0) in 1,4-dioxane T=90°C; 4 h;

1: acetophenone With tris-(dibenzylideneacetone)dipalladium(0); toluene-4-sulfonic acid hydrazide; lithium tert-butylate; 2-(dicyclohexylphosphino)-2',4',6'-tri-i-propyl-1,1’-biphenyl in 1,4-dioxane 0.0166667 h; Inert atmosphere; 2: meta-bromobenzonitrile in 1,4-dioxane T=110°C; 12 h; Inert atmosphere;

[hetba]Br; palladium (II) bromide in 1-methyl-pyrrolidin-2-one T=160°C; decarbonylative Heck olefination; 16 h;

thionyl chloride in dichloromethane 6 h; Heating; Yield given;

1: diethyl ether; benzene / Ambient temperature 2: thionyl chloride / CH2Cl2 / 6 h / Heating View Scheme

1: diethyl ether; benzene / Ambient temperature 2: thionyl chloride / CH2Cl2 / 6 h / Heating View Scheme

pyridine

1: 38 percent / 1,4-dicyanobenzene / acetonitrile / 10 °C / Irradiation 2: 1,4-dicyanobenzene / methanol; acetonitrile / 10 °C / Irradiation View Scheme